(6-fluoro-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone → (7-Bromo-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanol

HRID 1424461Notes

Reaction equation

HRID 1424461 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)=[N:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[O:13])=[N:9]2)=[CH:4][CH:3]=1.FC1C=C2C(=CC=1)N=C(C(C1C=CC(F)=CC=1)=O)N=C2NC1C=C(C)NN=1>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)=[N:7][C:8]([CH:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[OH:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 46893252(6-fluoro-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanoneHCID 46893255(7-bromo-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone

Product 1

HCID 46893256(7-Bromo-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanol

Procedure

(7-Bromo-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanol was prepared using a procedure analogous to that described in Example 54 substituting (7-bromo-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone from Example 56 (240 mg, 0.56 mmol) for the (6-fluoro-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone used in Example 54 (31 mg, 13%). 1H NMR (300 MHz, DMSO-d6) δ 12.17 (s, 1H), 10.55 (s, 1H), 8.54 (br s, 1H), 7.97 (br s, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.52-7.56 (m, 2H), 7.12-7.17 (m, 2H), 6.44 (s, 1H), 5.84 (s, 1H), 5.66 (s, 1H), 2.25 (s, 3H); LC-MS (ESI) m/z 428 (M+H)+.

Sources & evidence

ORD record
ord-fc6458c818d44136831d4f40f0e51c4a
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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