3-Methylpyrrolidin-3-ol → 4-(3-Hydroxy-3-methylpyrrolidin-1-yl)-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 525643Notes

Reaction equation

HRID 525643 reaction equation
F[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:22]1[S:26][CH:25]=[N:24][CH:23]=1.[CH3:27][C:28]1([OH:33])[CH2:32][CH2:31][NH:30][CH2:29]1>>[OH:33][C:28]1([CH3:27])[CH2:32][CH2:31][N:30]([C:2]2[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[O:7])=[CH:4][C:3]=2[C:22]2[S:26][CH:25]=[N:24][CH:23]=2)[CH2:29]1

Participants

3

Reactant 2

HCID 145784583-Methylpyrrolidin-3-olHCID 899067714-fluoro-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Product 1

HCID 899074994-(3-Hydroxy-3-methylpyrrolidin-1-yl)-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using 4-fluoro-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1) and 3-methylpyrrolidin-3-ol to afford a yellow solid. UPLC-MS (Condition 1) tR=2.57 min, m/z=464.1 [M+H]+, m/z=462.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.30 (m, 3H) 1.63-1.85 (m, 2H) 2.88 (s, 1H) 2.95 (s, 1H) 3.02-3.15 (m, 1H) 3.26-3.30 (m, 1H) 4.72 (s, 1H) 6.94 (d, J=8.80 Hz, 1H) 7.33 (d, J=9.05 Hz, 2H) 7.78-8.00 (m, 6H) 9.15 (s, 1H) 10.14 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-679267b9c74944d2bc347e6f88daf1b5
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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