3-Chloro-4-hydroxyphenylboronic Acid → HCID 178450285, compound

HRID 2271706Notes

Reaction equation

HRID 2271706 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.[Cl:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[OH:39]>>[Cl:32][C:33]1[CH:34]=[C:35]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]3[NH:17][C@H:18]2[CH2:19][CH2:20][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:22][CH2:23]2)[CH:36]=[CH:37][C:38]=1[OH:39]

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 178450270HCID 178450270, compound

Product 1

HCID 178450285HCID 178450285, compoundYield 72.5%

Procedure

Following general procedure D, tert-butyl trans-4-(6-bromo-3-isobutyrylquinolin-4-ylamino)cyclohexylcarbamate (49 mg, 0.100 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (34 mg, 0.200 mmol) to afford the desired product (39 mg, 72%) as an off-white solid: ESI MS m/z 538 [C30H36ClN3O4+H]+.

Sources & evidence

ORD record
ord-112519d7c9434ce4844e130cd6517f3c
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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