(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide → HCID 89907986, compound

HRID 923878Notes

Reaction equation

HRID 923878 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[CH:30]=[C:31]([C:44]([OH:47])([CH3:46])[CH3:45])[CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[F:28][C:29]1[CH:34]=[C:33]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:19])([F:20])[F:18])=[CH:14][CH:15]=2)=[O:8])[CH:32]=[C:31]([C:44]([OH:47])([CH3:45])[CH3:46])[CH:30]=1

Participants

3

Reactant 2

HCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamideHCID 899078292-[3-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propan-2-ol

Product 1

HCID 89907986HCID 89907986, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 53 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 2-(3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol and to afford a yellow resin. HPLC (Condition 4) tR=5.18 min, UPLC-MS (Condition 3) tR=1.10 min, m/z=520.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.43 (d, J=1.96 Hz, 6H) 1.65-1.75 (m, 1H) 1.76-1.89 (m, 1H) 2.86 (d, J=10.95 Hz, 1H) 3.13-3.28 (m, 2H) 3.34-3.50 (m, 1H) 4.03-4.22 (m, 1H) 4.82 (d, J=2.74 Hz, 1H) 5.19 (d, J=0.78 Hz, 1H) 7.09 (d, J=9.38 Hz, 1H) 7.18-7.28 (m, 2H) 7.33 (d, J=8.99 Hz, 2H) 7.77-7.88 (m, 2H) 7.98 (m, J=2.30, 0.80 Hz, 1H) 8.67-8.76 (m, 1H) 10.16 (s, 1H).

Workup

  1. customto afford a yellow resin

Sources & evidence

ORD record
ord-ea77f8a991bc43a88bd9451db8580215
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…