Simtuzumab → 3-Chloro-4-(6-hydroxyquinazolin-2-yl)benzoic acid

HRID 1472677Notes

Reaction equation

HRID 1472677 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[N:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([Cl:26])[CH:18]=1)([OH:16])=[O:15]>>[Cl:26][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1)[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 17750227SimtuzumabHCID 592548522-Chloro-6-methoxyquinazoline

Product 1

HCID 574071593-Chloro-4-(6-hydroxyquinazolin-2-yl)benzoic acid

Procedure

Prepared according to Scheme 6, B conditions, starting from Intermediate 8 and 4-carboxy-2-chlorophenylboronic acid. 1H NMR (DMSO-d6 400 MHz): δ 10.60 (brs, 1H), 9.56 (s, 1H), 8.10-7.89 (m, 4H), 7.62 (dd, J=9.2, 2.8 Hz, 1H), 7.38 (d, J=2.8 Hz, 1H). MS (ESI): m/z 300.8 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3cfd70826d3c40f6a398ce0c7c924280
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

Loading…