Hydrochloric Acid → (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one hydrochloride

HRID 2062150Notes

Reaction equation

HRID 2062150 reaction equation
[OH:1][C@H:2]([CH2:28][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][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].CCOCC.[ClH:37]>C(Cl)Cl>[ClH:37].[OH:1][C@H:2]([CH2:28][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][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 135525571(R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one

Product 1

HCID 136366759(R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one (265 mg, 0.63 mmol) in CH2Cl2 (3 mL) under inert atmosphere was added 10 mL of ether followed by the dropwise addition of 2 M HCl (0.315 mL, 0.63 mmol). The reaction was stirred for 30 min before the formed precipitate was filtered to afford (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-4-methylpentan-1-one hydrochloride (261 mg, 91%). LC/MS: m/z 421.3 (M+H)+ at 2.60 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.28 (dd, J=7.9, 1.6 Hz, 1H), 8.19 (d, J=8.4 Hz, 1H), 7.96 (d, J=3.9 Hz, 2H), 7.65 (m, 1H), 7.48 (m, 1H), 7.04 (m, 2H), 4.37 (m, 1H), 4.10 (m, 4H), 3.80 (m, 4H), 1.77 (m, 1H), 1.41 (m, 2H), 0.91 (dd, J=6.6, 3.1 Hz, 6H).

Workup

  1. filtrationwas filtered

Sources & evidence

ORD record
ord-7410f6ecbeef47a180251b5d375765bc
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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