L-Valinol → HCID 67960670, compound

HRID 570471Notes

Reaction equation

HRID 570471 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]([CH:26]([CH3:28])[CH3:27])[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])[CH:26]([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 640993L-ValinolHCID 509244533-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide

Product 1

HCID 67960670HCID 67960670, 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-3-methylbutan-1-ol instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 345 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.49 (1H, br. s.) 10.02 (1H, s) 7.99 (1H, d, J=5.47 Hz) 7.79 (1H, d, J=5.27 Hz) 7.57 (1H, d, J=8.98 Hz) 7.41 (1H, d, J=5.47 Hz) 7.29 (1H, dd, J=3.32, 2.34 Hz) 6.69 (1H, d, J=5.47 Hz) 6.42 (1H, dd, J=3.51, 1.56 Hz) 4.58 (1H, t, J=5.56 Hz) 3.80 (1H, dd, J=8.88, 6.74 Hz) 3.46 (2H, t, J=5.95 Hz) 1.85 (1H, dq, J=13.64, 6.78 Hz) 0.85 (3H, d, J=6.64 Hz) 0.78 (3H, d, J=6.83 Hz)

Sources & evidence

ORD record
ord-543f64e9936345e9b28cf4a7ab1c7eb1
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

Loading…