3-Amino-5-methyl-thiophene-2-carboxylic acid methyl ester → 5-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid

HRID 570390Notes

Reaction equation

HRID 570390 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:16]([OH:18])=[O:17])=[C:4]2[CH:3]=[CH:2]1.N[C:20]1C=C(C)SC=1C(OC)=O>>[CH3:20][C:14]1[S:13][C:12]([C:16]([OH:18])=[O:17])=[C:11]([NH:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:1][CH:2]=[CH:3][C:4]=23)[CH:15]=1

Participants

3

Reactant 2

HCID 8189523-Amino-5-methyl-thiophene-2-carboxylic acid methyl esterHCID 669574403-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acid

Product 1

HCID 669580045-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid

Procedure

This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid using methyl 3-amino-5-methylthiophene-2-carboxylate instead of methyl 3-aminothiophene-2-carboxylate. LCMS (ESI) 274 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (1H, br. s.) 9.66 (1H, s) 8.06 (1H, d, J=4.49 Hz) 7.30-7.38 (1H, m) 6.95 (1H, d, J=5.47 Hz) 6.42 (1H, d, J=1.76 Hz) 2.50 (3H, s)

Sources & evidence

ORD record
ord-c275df5b0a074fec9e17d84b1f5f2414
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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