Hydrochloric Acid → HCID 178481244, compound

HRID 928841Notes

Reaction equation

HRID 928841 reaction equation
[N:1]1([C:6]2[CH:40]=[CH:39][C:9]([CH2:10][C:11]3[C:12]([O:37]C)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([C:24]3[N:28]([CH3:29])[CH:27]=[N:26][CH:25]=3)[OH:23])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.Cl.[OH-].[Na+]>CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][C:11]3[C:12]([OH:37])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([OH:23])[C:24]3[N:28]([CH3:29])[CH:27]=[N:26][CH:25]=3)=[CH:16][CH:15]=4)=[CH:39][CH:40]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 74220546(3-(4-(1H-Pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol

Product 1

HCID 178481244HCID 178481244, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (3-(4-(1H-pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methanol (0.32 g, 0.561 mmol, Example 33A) in methanol (1.5 mL) was added 6.6 M aqueous HCl (5 mL). The resulting solution was stirred for 4 days, cooled in an ice bath and aqueous NaOH (3 M) added dropwise to a basic pH. The crude product was isolated by filtration then chromatographed (10% MeOH in DCM, gradient) to provide the product, 1H NMR (400 MHz, DMSO-d6) δ ppm 12.23 (s, 1H), 8.41 (d, J=2.5 Hz, 1H), 7.85 (s, 1H), 7.58-7.77 (m, 4H), 7.32-7.48 (m, 6H), 7.28 (d, J=9.1 Hz, 2H), 6.97 (s, 1H), 6.51 (d, J=2.0 Hz, 1H), 6.12 (s, 1H), 4.11 (s, 2H), 3.32 (s, 3H); MS (ESI) 556.

Workup

  1. temperaturecooled in an ice bath

Sources & evidence

ORD record
ord-fe99b6a2e08740b1b560791af722c68e
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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