3-(Trifluoromethyl)phenylboronic acid → 4-(3-methoxy-3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide

HRID 1473690Notes

Reaction equation

HRID 1473690 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][N:23]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][N:9]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>>[CH3:29][O:28][C:4]1[CH:3]=[C:2]([C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([C:31]([F:42])([F:41])[F:30])[CH:37]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][N:23]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 866877734-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide

Product 1

HCID 866877744-(3-methoxy-3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that of EXAMPLE 525, except that 4-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide and (3-(trifluoromethyl)phenyl)boronic acid were used as the coupling partners to afford 4-(3-methoxy-3′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)-N-(pyrimidin-4-yl)quinazoline-7-sulfonamide as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ=9.48 (s, 1H), 8.58 (s, 1H), 8.50 (s, 1H), 8.23 (br. s., 1H), 8.19-8.11 (m, 2H), 8.10-8.01 (m, 1H), 7.89 (d, J=8.8 Hz, 1H), 7.85-7.72 (m, 2H), 7.62-7.53 (m, 3H), 7.01 (br. s., 1H), 3.82 (s, 6H). m/z (ESI) 538.2 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that of EXAMPLE 525

Sources & evidence

ORD record
ord-392b6892537a477b9a4c2cd8d5c0fefc
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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