2-Bromo-3-fluorobenzoic acid → (2-Bromo-3-fluorophenyl)(5-(6-fluoroquinazolin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone

HRID 244020

Reaction equation

HRID 244020 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:19][CH:18]3[CH:14]([CH2:15][NH:16][CH2:17]3)[CH2:13]1)[N:6]=[CH:5]2.[Br:20][C:21]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24]>>[Br:20][C:21]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:16]1[CH2:17][CH:18]2[CH:14]([CH2:13][N:12]([C:7]3[N:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=4)[N:8]=3)[CH2:19]2)[CH2:15]1)=[O:24]

Participants

3

Reactant 2

HCID 3026222-Bromo-3-fluorobenzoic acidHCID 699391556-Fluoro-2-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)quinazoline

Product 1

HCID 67116195(2-Bromo-3-fluorophenyl)(5-(6-fluoroquinazolin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone

Procedure

The title compound was prepared in a manner analogous to Example 15, utilizing Intermediate 43 and 2-bromo-3-fluorobenzoic acid. MS (ESI): mass calculated for C21H17BrF2N4O, 458.1; m/z found 459.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.95 (d, J=19.8, 1H), 8.01 (s, 1H), 7.59 (dt, J=13.3, 6.7, 1H), 7.52-7.40 (m, 1H), 7.40-7.28 (m, 1H), 7.18-7.05 (m, 2H), 4.01 (dt, J=12.8, 8.4, 2H), 3.95-3.85 (m, 1H), 3.80-3.48 (m, 4H), 3.27-3.04 (m, 3H).

Sources & evidence

ORD record
ord-45552bc1918046a886aeb3b5a67f208a
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Linked notes

Loading…