HCID 66957844, compound → HCID 50925352, compound

HRID 570481Notes

Reaction equation

HRID 570481 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][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])[CH2:9]1)=O)(C)(C)C.N[C@@H:32]([C:36]1C=CC=C[CH:37]=1)[CH2:33][C:34]#N>>[C:12]([CH2:11][C@@H:10]([NH:13][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:9]1[CH:37]=[CH:36][CH:32]=[CH:33][CH:34]=1)#[N:8]

Participants

3

Reactant 2

HCID 66957844HCID 66957844, compoundHCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 50925352HCID 50925352, 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-phenylpropanenitrile (Organic Synthesis 2008, 85, 219-230) instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 388 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (1H, br. s.) 10.24 (1H, s) 8.79 (1H, d, J=8.44 Hz) 8.02 (1H, d, J=5.42 Hz) 7.85 (1H, d, J=5.47 Hz) 7.51 (1H, d, J=5.47 Hz) 7.44 (2H, d, J=7.18 Hz) 7.22-7.39 (4H, m) 6.84 (1H, d, J=5.47 Hz) 6.41 (1H, dd, J=3.47, 1.22 Hz) 5.46 (1H, td, J=8.63, 6.47 Hz) 3.01-3.22 (2H, m)

Sources & evidence

ORD record
ord-41b925353e8c4076abbd6ca40f0a3d3e
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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