Hydrochloric Acid → HCID 136366799, compound

HRID 2079300Notes

Reaction equation

HRID 2079300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:32])[C@H:26]([OH:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH2:20]1.CCOCC.[ClH:38]>C(Cl)Cl>[ClH:38].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:32])[C@H:26]([OH:31])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121409HCID 136121409, compound

Product 1

HCID 136366799HCID 136366799, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(4-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one (285 mg, 0.65 mmol) in CH2Cl2 (2 mL) under an N2 atmosphere was added ether (10 mL), followed by the dropwise addition of a 2 M HCl solution in ether (0.325 mL, 0.65 mmol). A precipitate was formed which was stirred for 30 min, collected by vacuum filtration, and dried to afford (R)-1-(4-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one hydrochloride (284 mg, 92%). LC/MS: m/z 439.30 (M+H)+ at 3.00 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)): 1H NMR (400 MHz, DMSO-d6) d 8.32 (dd, J=8.1, 1.5 Hz, 1H), 8.02 (m, 1H), 7.92 (dd, J=9.7, 2.7 Hz, 1H), 7.85 (m, 1H), 7.45 (m, 1H), 7.01 (m, 2H), 4.37 (dd, J=9.2, 4.1 Hz, 1H), 4.04 (m, 4H), 3.83 (m, 4H), 1.76 (m, 1H), 1.41 (m, 2H), 0.90 (dd, J=6.6, 3.7 Hz, 6H) ppm.

Workup

  1. customA precipitate was formed which
  2. filtrationcollected by vacuum filtration
  3. customdried

Sources & evidence

ORD record
ord-1928d84a22e447f3a6a0fdf29a6e3a75
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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