Hydrochloric Acid → HCID 136366883, compound

HRID 2079257Notes

Reaction equation

HRID 2079257 reaction equation
[OH:1][CH:2]([CH:29]([CH3:31])[CH3:30])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].CCOCC.[ClH:37]>C(Cl)Cl>[ClH:37].[OH:1][CH:2]([CH:29]([CH3:31])[CH3:30])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121332HCID 136121332, compound

Product 1

HCID 136366883HCID 136366883, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-3-methylbutan-1-one (230 mg, 0.54 mmol) in CH2Cl2 (3 mL) under an inert atmosphere was added ether (12 mL) followed by the dropwise addition of 2 M HCl solution in ether (0.27 mL, 0.54 mmol) which resulted in the formation of a precipitate which was stirred for an hour and then collected by vacuum filtration and dried to afford 2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-3-methylbutan-1-one hydrochloride (205 mg, 83%). LC/MS: m/z 421.3 (M+H)+ at 2.48 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) d 8.25 (d, J=7.9 Hz, 1H), 8.08 (d, J=8.5 Hz, 1H), 7.74 (s, 1H), 7.48 (t, J=6.6 Hz, 2H), 7.04 (m, 2H), 4.10 (m, 5H), 3.79 (m, 4H), 2.53 (s, 3H), 1.90 (m, 1H), 0.87 (dd, J=16.3, 6.7 Hz, 6H) ppm.

Workup

  1. customresulted in the formation of a precipitate which
  2. filtrationcollected by vacuum filtration
  3. customdried

Sources & evidence

ORD record
ord-156f96196eed47dabb70443ddb9c39e4
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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