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

HRID 1472668Notes

Reaction equation

HRID 1472668 reaction equation
Cl[C:2]1[CH:11]=[C:10]([F:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13]C)[CH:8]=2)[N:3]=1.[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[C:20]([Cl:27])[CH:19]=1)([OH:17])=[O:16]>>[Cl:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:2]1[CH:11]=[C:10]([F:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[CH:8]=2)[N:3]=1)[C:15]([OH:17])=[O:16]

Participants

3

Reactant 2

HCID 17750227SimtuzumabHCID 866899352-Chloro-4-fluoro-6-methoxyquinoline2×

Product 1

HCID 569590693-Chloro-4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid

Procedure

Followed Scheme 2, B conditions starting with 2-chloro-4-fluoro-6-methoxyquinoline (Intermediate 7) and 4-carboxy-2-chlorophenylboronic acid. 1H NMR (MeOD 400 MHz): δ 8.20 (d, J=1.2 Hz, 1H), 8.10 (dd, J=8.0, 1.6 Hz, 1H), 8.02 (d, J=9.2, 1.2 Hz, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.52-7.45 (m, 2H), 7.47 (d, J=2.4 Hz, 1H). MS (ESI): m/z 317.9 [M+H]+.

Sources & evidence

ORD record
ord-900e944ee1af43d6b577108f9fae5b7c
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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