phenylalaninol, (S)- → HCID 50924919, compound

HRID 570464Notes

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]([CH2:40][OH:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[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])[CH2:40][OH:41])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

Reactant 2

HCID 447213phenylalaninol, (S)-

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 50924919HCID 50924919, 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 (S)-phenylalaninol instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 393 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.13 (1H, s) 7.98 (1H, d, J=5.47 Hz) 7.72-7.82 (2H, m) 7.40 (1H, d, J=5.42 Hz) 7.28 (1H, dd, J=3.44, 2.32 Hz) 7.19 (4H, d, J=0.10 Hz) 7.10 (1H, td, J=5.93, 2.59 Hz) 6.73 (1H, d, J=5.52 Hz) 6.38 (1H, dd, J=3.42, 1.76 Hz) 4.82 (1H, t, J=5.66 Hz) 4.13 (1H, ddd, J=14.19, 5.60, 3.15 Hz) 3.42-3.51 (1H, m) 3.38 (1H, t, J=5.93 Hz) 2.84-2.93 (1H, m) 2.73 (1H, dd, J=13.64, 8.96 Hz)

Sources & evidence

ORD record: ord-ac89c1f1da2d4bc8be8d5ae02e286b1e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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