Hydrochloric Acid → (r)-1-(4-(6-Fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4,4-dimethylpentan-1-one hydrochloride

HRID 2062166Notes

Reaction equation

HRID 2062166 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:33])[C@H:26]([OH:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH2:20]1.[ClH:34].CCOCC>C(Cl)Cl>[ClH:34].[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:33])[C@H:26]([OH:32])[CH2:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121496(R)-1-(4-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4,4-dimethylpentan-1-one

Product 1

HCID 136366635(r)-1-(4-(6-Fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4,4-dimethylpentan-1-one hydrochlorideYield 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-4,4-dimethylpentan-1-one (230 mg, 0.51 mmol) in CH2Cl2 (3 mL) under an inert atmosphere was added dropwise a 2 M HCl solution in ether (0.255 mL, 0.51 mmol). To it was then added ether (15 mL) which resulted in formation of a precipitate that was allowed to stir for an hour. The product was collected by vacuum filtration and dried to afford (R)-1-(4-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4,4-dimethylpentan-1-one hydrochloride (230 mg, 92%). LCMS: m/z 453.5 (M+H)+ at 3.19 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.40 (dd, J=7.8, 1.4 Hz, 1H), 8.04 (m, 1H), 7.88 (m, 2H), 7.43 (m, 1H), 6.99 (m, 2H), 4.45 (dd, J=8.8, 3.0 Hz, 1H), 4.02 (m, 4H), 3.79 (m, 4H), 1.56 (m, 1H), 1.42 (m, 1H), 0.97 (s, 9H).

Workup

  1. filtrationThe product was collected by vacuum filtration
  2. customdried

Sources & evidence

ORD record
ord-40a9dbb7d5b64262a3e9d1ab12dda8fd
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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