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Quality Control of Methotrexate EP Impurity A Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Methotrexate EP Impurity A

CAS No. :	945-24-4
Formula :	C₇H₈N₆O
M.W :	192.18
SMILES Code :	OCC1=NC2=C(N)N=C(N)N=C2N=C1
MDL No. :	MFCD00006711
InChI Key :	CYNARAWTVHQHDI-UHFFFAOYSA-N
Pubchem ID :	70347

Safety of Methotrexate EP Impurity A

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of Methotrexate EP Impurity A

* 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 [ 945-24-4 ]

[ 945-24-4 ] Synthesis Path-Downstream 1~41

1
[ 945-24-4 ]
[ 10541-83-0 ]
[ 19741-14-1 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5146 - 5154.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 3503 - 3515.

2
[ 945-24-4 ]
[ 112113-84-5 ]
[ 112113-77-6 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 763 - 768.

3
[ 945-24-4 ]
[ 158090-74-5 ]
[ 1053629-25-6 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2167 - 2174.

4
[ 945-24-4 ]
[ 52853-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine dibromide; N,N-dimethyl acetamide; at 20℃; for 200h;	<strong>[945-24-4]2,4-diamino-6-(hydroxymethyl)pteridine</strong> hydrochloride (4.40 g; 19.19 mmol) was dissolved in hot water (150 mL) and the solution was neutralized by addition of 1 M NaOH (ca. 20 mL). The precipitate was filtered, washed with water, and dried in vacuo over P2O5. Subsequently, this was suspended in DMAc (25 mL), and triphenylphosphine dibromide (18.12 g; 42.92 mmol) was added. The turbid reaction mixture was stirred for 20 hr at 200C. 4-(Methylamino)benzoic acid (2.95 g; 19.50 mmol) and DIPEA (5.04 g; 39.00 mmol) were added, and the turbid reaction mixture was stirred for 3 days at 200C. Then, it was poured in 0.33 M NaOH-solution (250 mL), the precipitate was filtered off, and the filtrate was neutralized by addition of 10% acetic acid in water (ca. 20 mL). The precipitate was filtered, washed with water, triturated with methanol (30 mL), and dried in vacuo over P2O5, to yield the product as a beige/orange powder (3.48 g; 56%).1H-NMR (DMSO): delta 8.59 (s, IH), 7.53 (d, 2H, 8.8 Hz), 7.7 (br. s, IH), 7.5 (br. s, IH), 6.83 (d, 2H, 8.8 Hz), 4.79 (s, 2H), 3.23 (s, 3H) ppm. FT-IR (ATR): V 3335, 3194, 2964, 1651, 1597, 1292, 1187 cm"1.

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 660 - 667.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 3455 - 3462.
[3]Patent: WO2007/110811,2007,A2 .Location in patent: Page/Page column 23.

5
[ 52-89-1 ]
[ 5392-28-9 ]
[ 945-24-4 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5146 - 5154.

6
[ 945-24-4 ]
(S)-2-[4-(2,4-Diamino-pteridin-6-ylmethoxycarbonyl)-benzoylamino]-pentanedioic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3455 - 3462.

7
[ 945-24-4 ]
[ 581785-35-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3455 - 3462.

8
[ 712-29-8 ]
[ 945-24-4 ]

References: [1]Helvetica Chimica Acta,2003,vol. 86,p. 1 - 12.

9
[ 32363-58-9 ]
[ 945-24-4 ]

References: [1]Helvetica Chimica Acta,2003,vol. 86,p. 1 - 12.

10
[ 945-24-4 ]
1,12-d-[4-(4S)-carboxy-4-{4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoylamino}butyrylamino]dodecane [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 1501 - 1507.

11
[ 945-24-4 ]
[ 56892-87-6 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5146 - 5154.

12
[ 945-24-4 ]
[ 357933-50-7 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5146 - 5154.

13
[ 945-24-4 ]
2-[[[3-carboxy-3-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]amino]propyl]hydroxyphosphinyl]methyl]pentane-1,5-dioic acid tetra(triethylamine) salt [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5146 - 5154.

14
[ 945-24-4 ]
(S)-2-{4-[(3-Carboxy-propyl)-(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoyloxy}-pentanedioic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

15
[ 945-24-4 ]
(S)-2-{4-[(4-Carboxy-butyl)-(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoyloxy}-pentanedioic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

16
[ 945-24-4 ]
(S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-(3-ethoxycarbonyl-propyl)-amino]-benzoyloxy}-pentanedioic acid diethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

17
[ 945-24-4 ]
(S)-2-{4-[(5-Carboxy-pentyl)-(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoyloxy}-pentanedioic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

18
[ 945-24-4 ]
(S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-(4-ethoxycarbonyl-butyl)-amino]-benzoyloxy}-pentanedioic acid diethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

19
[ 945-24-4 ]
(S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-(5-ethoxycarbonyl-pentyl)-amino]-benzoyloxy}-pentanedioic acid diethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1463 - 1468.

20
[ 945-24-4 ]
[ 156579-02-1 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

21
[ 945-24-4 ]
[ 156579-01-0 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

22
[ 52853-40-4 ]
[ 945-24-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

23
[ 191786-01-3 ]
[ 945-24-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

24
[ 191786-03-5 ]
[ 945-24-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

25
[ 191786-02-4 ]
[ 945-24-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 363 - 368.

26
[ 945-24-4 ]
[ 67022-39-3 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.

27
[ 945-24-4 ]
[ 79640-75-8 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.

28
[ 945-24-4 ]
[ 79648-88-7 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.

29
[ 945-24-4 ]
[ 121788-83-8 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.

30
[ 945-24-4 ]
[ 121788-84-9 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 2426 - 2431.

31
[ 945-24-4 ]
[ 43111-51-9 ]