HCID 28186523, compound → HCID 50925356, compound

HRID 570482Notes

Reaction equation

C(OC(N1CCC(N[C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])C1)=O)(C)(C)C.[NH2:31][C@@H:32]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:33][C:34]([NH2:36])=[O:35]>>[C:34]([CH2:33][C@@H:32]([NH:31][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[NH:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12)=[O:15])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:35])[NH2:36]

Participants

Reactant 2

HCID 28186523HCID 28186523, compound

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

Product 1

HCID 50925356HCID 50925356, compound

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 (3R)-3-amino-3-phenylpropanamide instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 406 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.22 (1H, s) 8.65 (1H, d, J=8.44 Hz) 8.01 (1H, d, J=5.42 Hz) 7.80 (1H, d, J=5.47 Hz) 7.47 (1H, d, J=5.52 Hz) 7.33-7.39 (3H, m) 7.26-7.32 (4H, m) 7.17-7.23 (1H, m) 6.86 (1H, br. s.) 6.80 (1H, d, J=5.86 Hz) 6.40 (1H, d, J=3.56 Hz) 5.44 (1H, q, J=7.24 Hz) 2.66-2.75 (1H, m) 2.57-2.65 (1H, m)

Sources & evidence

ORD record: ord-c4b163343b2d4012a3ebfffe7f9641bd
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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