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Chemical Structure| 594-45-6
Chemical Structure| 594-45-6
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CAS No. :594-45-6 MDL No. :MFCD00007529
Formula : C2H6O3S Boiling Point : -
Linear Structure Formula :- InChI Key :CCIVGXIOQKPBKL-UHFFFAOYSA-N
M.W : 110.13 Pubchem ID :11668
Synonyms :

Safety of [ 594-45-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 UN#:2586
Hazard Statements:H314 Packing Group:
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Application In Synthesis of [ 594-45-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 594-45-6 ]
  • Downstream synthetic route of [ 594-45-6 ]

[ 594-45-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 594-45-6 ]
  • [ 149-73-5 ]
  • [ 1912-28-3 ]
Reference: [1] Synthetic Communications, 1985, vol. 15, # 12, p. 1057 - 1062
  • 2
  • [ 656247-17-5 ]
  • [ 594-45-6 ]
  • [ 656247-18-6 ]
YieldReaction ConditionsOperation in experiment
100% for 4 h; Reflux Three 25ml flask were added successively 2.0g Trinidad Technip, 7.5g ethanesulfonic acid, 10ml methanol was heated to reflux, stirred at reflux for 4h, heating was stopped, the solvent was evaporated to dryness, the resulting solid was slurried add 15ml of acetone, suction filtered to give a pale yellow solid 2.4g, yield: 100percent.Purity by HPLC: 99.75percent
97.3% at 60℃; Example 8: Synthesis of the 3-Z-[1 -(4-(N-((4-methyl-piperazin-1 -yl)- methylcarbonyl)-N-methyl-amino)-anilino)-1 -phenyl-methylene]-6- <n="27"/>methoxycarbonyl-2-indolinone, monoethanesulfonate"ANILINO" 3-Z-[1-(4-(N-((4-methyl-pιperazιn-1-yl)-methylcarbonyl)-N-me thyl-amιno)-anιlιno)-1-phenyl-methylene]-6-methoxycarbonyl- 2-ιndolιnone, monoethanesulfonateA suspension of 3-Z-[1 -(4-(N-((4-methyl-piperazin-1 -yl)-methylcarbonyl)-N- nnethyl-annino)-anilino)-1 -phenyl-nnethylene]-6-nnethoxycarbonyl-2-indolinone (30,0 g; 0,055 mol) in methanol (200 ml) and water (2,4 ml) is heated to 60 0C. Aqueous ethanesulfonic acid (70percent (w/w); 8,75 g; 0,056 mol) is added to the reaction mixture. The resulting solution is cooled to 50 0C, seeded and then diluted with isopropanol (200 ml). The mixture is further cooled to 0 0C and stirred for 2 h at this temperature. The precipitate is isolated, washed with isopropanol (120 ml) and dried to furnish 35,1 g (97,3 percent) of the monoethanesulfonate salt of the compound as yellow crystals. 1H-NMR (400 MHz, DMSO-de) δ: 12,26 (s, 11-H); 10,79 (s, 1 H, 1 -H); 9,44 (s, 1 H, 24-H); 7,64 (m, 1 H, 32-H); 7,59 (m, 2 H, 31 -H + 33-H); 7,52 (m, 2 H, 30-H + 34-H); 7,45 (d, J = 1 ,6 Hz, 1 H, 7-H); 7,20 (dd, J = 8,2; 1 ,6 Hz, 1 H, 5-H); 7,16 (m, 2 H, 14-H + 16-H); 6,90 (m, 2 H, 13-H + 17-H); 5,85 (d, J = 8,2 Hz, 1 H, 4-H); 3,78 (s, 3 H, 37-H3); 3,45 - 2,80 (broad m, 4 H, 23-H2 + 25-H2); 3,08 (s, 3 H, 28-H3); 2,88 (s, 2 H, 20-H2); 2,85 - 2,30 (broad m, 4 H, 22-H2 + 26-H2); 2,75 (s, 3 H, 27-H3); 2,44 (q, J = 7,4 Hz, 2 H, 39-H2); 1 ,09 (t, J = 7,4 Hz, 3 H, 38-H3). 13C-NMR (126 MHz, DMSO-de) δ: 9,8 (C-38); 36,6 (C-28); 42,3 (C-27); 45,1 (C-39); 51 ,7 (C- 37); 48,9 (C-22 + C-26); 52,6 (C-23 + C-25); 57,5 (C-20); 97,7 (C-3); 109,5 (C- 7); 1 17,3 (C-4); 121 ,4 (C-5); 123,8 (C-13 + C-17); 124,1 (C-6); 127,7 (C-14 + C- 16); 128,4 (C-30 + C-34); 128,8 (C-9); 129,5 (C-31 + C-33); 130,5 (C-32); 132,0 (C-29); 168,5 (C-9); 136,3 (C-8); 137,3 (C-12); 139,5 (C-15); 158,1 (C-10); 166,3 (C-35); 168,0 (C-19); 170,1 (C-2). MS (m/z): 540 (M(base) + H)+. Anal. <n="28"/>calcd. for C33H39N5O7S: C, 60.17; H, 6.12; N, 10.63; S, 4.87. Found: C, 60.40; H, 6.15; N, 10.70; S, 4.84.
95% at 0 - 65℃; for 1 h; To a Suspension of (Z)-methyl-3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl) acetami- de)-phenyl) amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate 6 (36 g, 0.066 mol) in methanol (237 mL) and water (2.88 mL) ethanesulfonic acid (7.92 g 0.0719 mol) in water (2.88 mL) was added at 60-65°C. The resulting suspension was cooled to 50C, and was diluted with isopropanol (237 mL). The reaction mixture was cooled to 0C and stirred for 1h. The precipitate obtained was filtered and washed with mixture of methanol and isopropanol (50percent) (50 ml), product was dried to obtain crude Nintedanib monoethane sulfonate (36.6 g) which was crystallized from methanol (5 Vol) to obtain pure Nintedanib monoethane sulfonate salt as yellow crystals (33 g) (HPLC purity >99percent). DSC: 298C; IR (KBr, cm-1): 3321, 3273, 1710, 1652, 1615, 1515, 1435, 1378, 1289, 1209, 1161, 1087; 1H-NMR (400 MHz, DMSO): δ 1.08 (t, 3H, J = 7.31 Hz), 2.41-2.47 (q, 2H), 2.50-3.16 (broad m, 13H), 3.37 (s, 3H), 3.76 (s, 3H), 5.82 (d, 1H, J = 7.88Hz), 6.87 (d, 2H, J = 7.36 Hz), 7.14-7.20 (m, 3H), 7.49 (s, 1H), 7.49 (d, 2H, J = 6.68 Hz), 7.56-7.63 (m, 3H), 9.45 (s, 1H), 10.99 (s, 1H), 12.25 (s, 1H), 13C-NMR (100 MHz, DMSO): δ 37.15, 42.79, 45.65, 49.40, 52.26, 53.10, 58.04, 98.25, 110.01, 117.78, 121.97, 124.32, 124.59, 128.27, 128.90, 129.36, 130.00, 131.00, 132.52, 136.79, 137.93, 140.00, 158.66, 166.85, 168.47 and 170.65; MS: m/z 540 [M]+1.
89.7% at 50℃; 500 grams of the crystalline compound of Example 5 is suspended in 10 liters of ethanol, heated to 50 ° C and 180 grams of 70percent aqueous ethanesulfonic acid are added. The resulting solution was cooled to 40 ° C,An additional 4.5 liters of t-butyl ether was added. Crystallize after a few minutes. To achieve complete precipitation, the mixture was stirred for a further 16 hours at room temperature. After cooling to 10 ° C, suction filtration, washing with 2 t-butyl ether and drying under vacuum at 40 ° C,Ethanesulfonate compounds are obtained.Yield: 538 g (89.7percent yield).
87.6% at 50℃; 605 [G] (1.12 mol) of [3-Z- [1- (4- (N- ( (4-METHYL-PIPERAZIN-1-YL)-METHYLCARBONYL)-N-METHYL-] [AMINO)-ANILINO)-1-PHENYL-METHYLENE]-6-METHOXYCARBONYL-2-INDOLINONE] are suspended in 9 litres of methanol and heated to [50°C.] 183.7 [G] (1.121 mol) of 70percent aqueous [ETHANESULPHONIC] acid are added. The solution obtained is cooled to [40°C] and 4. 5 litres of [TERT.-BUTYLMETHYLETHER] are added. After a few minutes crystallisation sets in. To achieve total precipitation the mixture is stirred for another 16 hours at ambient temperature. After cooling to [10°C] it is suction filtered, washed with 2 litres of tert.- butylmethylether and dried [AT 40°C IN VACUO.] Yield : 638 g (87.6percent of theory) Tm. [P.] = 305 [5°C] (DSC 1 OK/min) Purity according to HPLC: 99.4percent Water content: 1.0 to 2.0percent (KF)
80% at 60 - 65℃; Suspension of (Z)-methyl-3-(((4-(N-methyl-2-(4-methylpiperazin-l-yl)acetamide)phenyl) amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (36 gm, 0.066 mol) in methanol (237 ml) and water (2.88 ml)was heated to 60-65°C and aq. ethane sulfonic acid was added to the reaction mixture. The resulting solution was cooled to 50°C, seeds diluted with isopropanol (237 ml) was added. The reaction mixture was cooled at 0°C for lhr. Filtered the precipitate, washed with mixture of methanol and isopropanol (50 ml), dried to obtain crude Nintedanib monoethane sulfonate (36.6 gm) and crystallized from methanol (5 Vol) to obtained pure Nintedanib monoethane sulfonate salt as yellow crystals (33 gm) (80percent) (HPLC purity >99percent). DSC: 298°C; IR (KBr, cm-1): 3321, 3273, 1710, 1652, 1615, 1515, 1435, 1378, 1289, 1209, 1161, 1087; 1H-NMR (400 MHz, DMSO): δ 1.08 (t, 3H, J = 7.31 Hz), 2.41-2.47 (q, 2H), 2.50-3.16 (broad m, 13H), 3.37 (s, 3H), 3.76 (s, 3H), 5.82 (d, 1H, J = 7.88Hz), 6.87 (d, 2H, J = 7.36 Hz), 7.14-7.20 (m, 3H), 7.49 (s, 1H), 7.49 (d, 2H, J = 6.68 Hz), 7.56-7.63 (m, 3H), 9.45 (s, 1H), 10.99 (s, 1H), 12.25 (s, 1H), 13C-NMR (100 MHz, DMSO): δ 37.15, 42.79, 45.65, 49.40, 52.26, 53.10, 58.04, 98.25, 110.01, 117.78, 121.97, 124.32, 124.59, 128.27, 128.90, 129.36, 130.00, 131.00, 132.52, 136.79, 137.93, 140.00, 158.66, 166.85, 168.47 and 170.65; MS: m/z 540[M]+1.

Reference: [1] Patent: CN105418483, 2016, A, . Location in patent: Paragraph 0047; 0048
[2] Patent: WO2009/71523, 2009, A1, . Location in patent: Page/Page column 4; 25-27
[3] Synthetic Communications, 2017, vol. 47, # 10, p. 975 - 981
[4] Patent: CN104844499, 2017, B, . Location in patent: Paragraph 0078; 0079
[5] Patent: WO2004/13099, 2004, A1, . Location in patent: Page 13-14
[6] Patent: WO2016/178064, 2016, A1, . Location in patent: Page/Page column 27; 28
[7] Patent: EP1473043, 2004, A1, . Location in patent: Page 7
[8] Patent: CN106432042, 2017, A, . Location in patent: Paragraph 0041; 0042; 0043; 0044; 0045; 0046
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