N-Benzylethylenediamine → 5-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-benzylamino-ethyl)-amide

HRID 570457Notes

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.[CH3:42][C:43]1[S:47][C:46]([C:48](O)=[O:49])=[C:45]([NH:51][C:52]2[CH:57]=[CH:56][N:55]=[C:54]3[NH:58][CH:59]=[CH:60][C:53]=23)[CH:44]=1>>[CH2:31]([NH:38][CH2:39][CH2:40][NH:41][C:48]([C:46]1[S:47][C:43]([CH3:42])=[CH:44][C:45]=1[NH:51][C:52]1[CH:57]=[CH:56][N:55]=[C:54]2[NH:58][CH:59]=[CH:60][C:53]=12)=[O:49])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Reactant 3

HCID 77801N-Benzylethylenediamine

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

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

Product 1

HCID 707956465-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-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 5-Methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid instead of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid. LCMS (ESI) 406 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (1H, br. s.) 10.39 (1H, s) 8.02 (1H, d, J=5.42 Hz) 7.87 (1H, t, J=5.54 Hz) 7.26-7.36 (7H, m) 7.18-7.26 (1H, m) 6.83 (1H, d, J=5.47 Hz) 6.42 (1H, dd, J=3.47, 1.85 Hz) 3.76 (2H, s) 3.36 (2H, q, J=6.30 Hz) 2.69 (2H, t, J=6.39 Hz)

Sources & evidence

ORD record: ord-c9e5e271630d45b6aeb9973e6ece7296
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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