209286-73-7|1-Chloro-6-methylisoquinoline| Ambeed

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Quality Control of [ 209286-73-7 ] Purity: 97% SDS Specification

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Product Details of [ 209286-73-7 ]

CAS No. :	209286-73-7
Formula :	C₁₀H₈ClN
M.W :	177.63
SMILES Code :	CC1=CC2=C(C=C1)C(Cl)=NC=C2
MDL No. :	MFCD11110400
InChI Key :	VBKBNFQWNBALDD-UHFFFAOYSA-N
Pubchem ID :	21927769

Safety of [ 209286-73-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 209286-73-7 ]

* 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.

Downstream synthetic route of [ 209286-73-7 ]

[ 209286-73-7 ] Synthesis Path-Downstream 1~11

1
[ 131002-10-3 ]
[ 209286-73-7 ]

Yield	Reaction Conditions	Operation in experiment
67.4%	With trichlorophosphate; for 3.0h;Heating / reflux;	10.0 g of meta-tolyl-acrylic acid (61.7 mmole) was suspended in 50 ml of benzene, 12.6 mL of DPPA (0.95 eq) was added followed by 10.3 mi of triethylamine (1.2 eq). The resulted solution was stirred at room temperature for1 hr. The volatile was removed under vacuum and the meta-tolyl-acryloyl azide was purified by flash chromatograph to yield 11.5 g of pure compound (quantitative). This material, in 100 mL of diphenylmethane, was introduced dropwise into 100 ml of diphenylmethane previously heated up to200 C over a period of an hr. The resulted solution was kept at this temperature for another 4 hour then cooled down to room temp.. White precipitate was formed, it was filtered off. The solid was washed with hexanes three times and dried. The filtrate was diluted with 200 mi of hexanes, the solution was left standing overnight to allow for separation of the second crop. The materials were combined to give 4.2 g of6-methyl-isoquinolin-1-ol(50%). LC/MS rt-min (MH+) : 1.31 (160) [methodB].'H NMR (400 MHz, CD30D)8 ppm 2.49 (s, 3 H) 6.61 (d, J=7. 32 Hz,1 H) 7.13 (d, J=7. 02 Hz,1 H) 7.36 (d, J=8. 24 Hz, 1 H) 7.45 (s,1 H) 8.18 (d, J=8. 24 Hz, 1 H). The material was suspended in 15ml of POC13 and brought to reflux for 3 hours. After removal of the POC13 in vacuo, the residue was partitioned between EtOAc(1L), and cold aqueous NaOH (generated from1. ON 200 mL NaOH and 20 mL 10.0 N NaOH) and stirred for 15 min. The organic layer was washed with water (2 x 200 mL), brine (200 mL), dried(MgS04), and concentrated in vacuo to supply 1-chloro-6-methyl-isoquinoline (67.4%). LC/MS rt-min (MH+) : 1.92 (178) [methodB].'H NMR (400 MHz, CHLOROFORM-D)8 ppm 2.53 (s, 3 H) 7.47 (d, J=6. 11 Hz, 2 H) 7.56 (s,1 H) 8.18 (m, 2 H). The final alkylation of 1-chloro-6- methyl-isoquinoline with the tripeptide was carried out using the protocol described previously (Example 184). BOCNH-P3 (L-tert-BuGly)-P2 [(4R)-(6-methyl isoquinolin-1-oxo)-S-proline]- PI (1R, 2SVinyl Acca)-CONHSO2-Cyclopropane : the material was obtained as a white foam in 18% yield. LC/MSRt-min(MNa+) [method B]: 2.64 (720). 1H NMR (400 MHz, CD30D)8 ppm 1.05 (m, 13 H) 1.23 (m, 9 H) 1.42 (m, 1 H) 1.86 (dd, J=7. 95,5. 50 Hz,1 H) 2.25 (m, 2 H) 2.49 (s, 3 H) 2.61 (dd,J=13. 82,6. 48 Hz,1 H) 2.93 (m,1 H) 4.05 (dd, J=11. 86,3. 30 Hz,1 H) 4.23 (s,1 H) 4.43 (d, J=11. 49 Hz,1 H) 4.52 (m, 1 H) 5.10 (d, J=11. 49 Hz,1 H) 5.28 (d,J=17. 12 Hz,1 H) 5.74 (m,1 H) 5.83 (s,1 H) 7.24 (d, J=5. 87 Hz,1 H) 7.35(d, J=8. 07 Hz,1 H) 7.58 (s,1 H) 7.89 (d, J=5. 87 Hz,1 H) 8.07 (d, J=8. 56 Hz,1 H).

References: [1]Patent: WO2003/99274,2003,A1 .Location in patent: Page 292-293.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4568 - 4574.

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[ 209286-73-7 ]
[ 234109-25-2 ]