(S(R,R))-2-amino-1-phenylpropane-1,3-diol → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((1S,2S)-2-hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-amide

HRID 570462Notes

Reaction equation

C(OC(N1CCC([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])C1)=O)(C)(C)C.N[C@@H:32]([CH2:41][OH:42])[C@H:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[OH:34]>>[OH:34][C@@H:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@@H:32]([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])[CH2:41][OH:42]

Participants

Reactant 2

HCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diol

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 669577973-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid ((1S,2S)-2-hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-amide

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 (1S,2S)-2-amino-1-phenyl-1,3-propanediol instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 409 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (1H, br. s.) 9.67 (1H, s) 7.99 (1H, d, J=5.37 Hz) 7.76 (1H, d, J=5.32 Hz) 7.45 (1H, d, J=8.64 Hz) 7.33 (1H, d, J=5.37 Hz) 7.27 (1H, dd, J=3.54, 2.22 Hz) 7.21-7.25 (2H, m) 7.10-7.21 (3H, m) 6.62 (1H, d, J=5.42 Hz) 6.36 (1H, dd, J=3.54, 1.73 Hz) 5.55 (1H, d, J=4.73 Hz) 4.90 (1H, dd, J=4.83, 3.17 Hz) 4.84 (1H, t, J=5.64 Hz) 4.07 (1H, dt, J=7.80, 5.30 Hz) 3.50 (1H, dt, J=10.58, 6.96 Hz) 3.40 (1H, dt, J=10.55, 5.34 Hz)

Sources & evidence

ORD record: ord-a5a08be04af945468d99b8411f4ad9af
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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