L-Leucinol → HCID 66957586, compound

HRID 570472Notes

Reaction equation

HRID 570472 reaction equation
NCCN[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6].[NH2:22][C@@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25]>>[OH:25][CH2:24][C@@H:23]([NH:22][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6])[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 111307L-LeucinolHCID 509244533-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide

Product 1

HCID 66957586HCID 66957586, compound

Procedure

This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using (2S)-2-amino-4-methylpentan-1-ol instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 359 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, br. s.) 10.23 (1H, s) 8.00 (1H, d, J=5.37 Hz) 7.78 (1H, d, J=5.37 Hz) 7.62 (1H, d, J=8.59 Hz) 7.45 (1H, d, J=5.37 Hz) 7.30 (1H, dd, J=3.12, 1.85 Hz) 6.75 (1H, d, J=5.47 Hz) 6.42 (1H, d, J=2.73 Hz) 4.68 (1H, t, J=5.66 Hz) 4.05 (1H, td, J=9.42, 4.39 Hz) 3.36-3.47 (1H, m) 1.46-1.63 (1H, m, J=13.76, 6.82, 6.82, 6.65, 6.65 Hz) 1.23-1.45 (2H, m, J=13.36, 9.07, 9.07, 8.92, 4.59 Hz) 0.83 (6H, dd, J=6.54, 4.30 Hz)

Sources & evidence

ORD record
ord-33faa63f9d9d411ca4b5756eee5dbc7f
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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