2-Amino-2-phenylethan-1-ol → 5-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylicacid ((S)-2-hydroxy-1-phenyl-ethyl)-amide

HRID 570458Notes

Reaction equation

HRID 570458 reaction equation
C(OC(N1CCC(NC(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)C1)=O)(C)(C)C.[C:31]1([C@@H:37]([CH2:39][OH:40])[NH2:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH3:41][C:42]1[S:46][C:45]([C:47](O)=[O:48])=[C:44]([NH:50][C:51]2[CH:56]=[CH:55][N:54]=[C:53]3[NH:57][CH:58]=[CH:59][C:52]=23)[CH:43]=1.N1C2=NC=CC(NC3C=CSC=3C(O)=O)=C2C=C1>>[OH:40][CH2:39][C@@H:37]([NH:38][C:47]([C:45]1[S:46][C:42]([CH3:41])=[CH:43][C:44]=1[NH:50][C:51]1[CH:56]=[CH:55][N:54]=[C:53]2[NH:57][CH:58]=[CH:59][C:52]=12)=[O:48])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 1347972-Amino-2-phenylethan-1-olHCID 669574403-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acidHCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 669580045-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid

Product 1

HCID 669580225-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylicacid ((S)-2-hydroxy-1-phenyl-ethyl)-amide

Procedure

This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using (S)-2-phenylglycinol instead of 1-BOC-3-aminopyrrolidine and 5-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid. LCMS (ESI) 393 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.26 (1H, s) 8.12 (1H, d, J=8.05 Hz) 8.01 (1H, d, J=5.42 Hz) 7.31-7.38 (2H, m) 7.25-7.31 (4H, m) 7.17-7.24 (1H, m) 6.79 (1H, d, J=5.47 Hz) 6.39 (1H, dd, J=3.54, 1.98 Hz) 5.07 (1H, td, J=7.71, 5.76 Hz) 4.90 (1H, t, J=5.76 Hz) 3.56-3.74 (2H, m, J=11.13, 11.13, 10.97, 5.76 Hz) 2.52 (3H, d, J=1.07 Hz)

Sources & evidence

ORD record
ord-cf1991ec98924bcd92910336840b52bf
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

Loading…