1-BOC-3-Aminopiperidine → 3-{[2-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-3-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13]C(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCCC(N)C1)(OC(C)(C)C)=O.[NH:45]1[C:49]2=[N:50][CH:51]=[CH:52][C:53]([NH:54][C:55]3[S:56][CH:57]=[CH:58][C:59]=3[C:60]([OH:62])=O)=[C:48]2[CH:47]=[CH:46]1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:60]([C:59]2[CH:58]=[CH:57][S:56][C:55]=2[NH:54][C:53]2[CH:52]=[CH:51][N:50]=[C:49]3[NH:45][CH:46]=[CH:47][C:48]=23)=[O:62])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 3
Product 1
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 1-BOC-3-aminopiperidine 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) 428 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.85 (1H, br. s.) 11.67 (1H, br. s.) 8.28 (1H, d, J=6.83 Hz) 8.15 (1H, d, J=5.42 Hz) 7.57 (1H, d, J=5.81 Hz) 7.38 (1H, dd, J=3.27, 2.68 Hz) 6.99 (1H, d, J=5.47 Hz) 6.93 (1H, d, J=6.05 Hz) 6.47 (1H, dd, J=3.49, 1.88 Hz) 4.40-4.59 (1H, m, J=12.24, 6.09, 6.09, 5.83 Hz) 3.51-3.64 (1H, m) 3.41 (1H, t, J=7.74 Hz) 3.21 (1H, td, J=9.91, 5.52 Hz) 2.06-2.19 (1H, m) 1.90 (1H, td, J=11.17, 6.61 Hz) 1.41 (9H, br. s.)
Sources & evidence
- ORD record
- ord-355c69345d5548d5b9cb2ec56136df32
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023847B2
Reaction notes
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