N-Benzylethylenediamine → 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid (2-benzylamino-ethyl)-amide

HRID 570452Notes

Reaction equation

HRID 570452 reaction equation
C(OC(N1CCC(NC(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)C1)=O)(C)(C)C.[CH2:31]([NH:38][CH2:39][CH2:40][NH2:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[NH:42]1[C:46]2=[N:47][CH:48]=[CH:49][C:50]([NH:51][C:52]3[S:53][CH:54]=[CH:55][C:56]=3[C:57](O)=[O:58])=[C:45]2[CH:44]=[CH:43]1>>[CH2:31]([NH:38][CH2:39][CH2:40][NH:41][C:57]([C:56]1[CH:55]=[CH:54][S:53][C:52]=1[NH:51][C:50]1[CH:49]=[CH:48][N:47]=[C:46]2[NH:42][CH:43]=[CH:44][C:45]=12)=[O:58])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 77801N-BenzylethylenediamineHCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 669579912-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid

Product 1

HCID 509247642-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid (2-benzylamino-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 N-benzylethylenediamine instead of 1-BOC-3-aminopyrrolidine and 2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carboxylic acid instead of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid. LCMS (ESI) 392 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (1H, br. s.) 11.66 (1H, br. s.) 8.27 (1H, t, J=5.73 Hz) 8.15 (1H, d, J=5.52 Hz) 7.48 (1H, d, J=5.86 Hz) 7.25-7.39 (6H, m) 7.15-7.24 (1H, m) 6.98 (1H, d, J=5.47 Hz) 6.92 (1H, d, J=0.10 Hz) 6.46 (1H, dd, J=3.42, 1.76 Hz) 3.73 (2H, s) 3.41 (2H, q, J=6.44 Hz) 2.68 (2H, t, J=6.56 Hz)

Sources & evidence

ORD record
ord-1e661e69ee784e458458defea002c0e1
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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