Methyl DL-serinate → HCID 66957380, compound

HRID 570463Notes

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.[CH3:31][O:32][C:33](=[O:38])[CH:34]([NH2:37])[CH2:35][OH:36]>>[CH3:31][O:32][C:33](=[O:38])[CH:34]([NH:37][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])[CH2:35][OH:36]

Participants

Reactant 2

HCID 416960Methyl DL-serinate

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 66957380HCID 66957380, 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 2-amino-3-hydroxy-propionic acid methyl ester instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 361 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (1H, br. s.) 10.09 (1H, s) 8.13 (1H, d, J=7.57 Hz) 8.03 (1H, d, J=5.56 Hz) 7.85 (1H, d, J=5.42 Hz) 7.46 (1H, d, J=5.42 Hz) 7.32 (1H, dd, J=3.22, 2.64 Hz) 6.80 (1H, d, J=5.56 Hz) 6.43 (1H, dd, J=3.39, 1.78 Hz) 5.06 (1H, t, J=6.05 Hz) 4.56 (1H, dt, J=7.53, 5.02 Hz) 3.72-3.83 (2H, m) 3.63 (3H, s)

Sources & evidence

ORD record: ord-5ad10fc2a7a543cb9503af415470a54b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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