tert-Butyl 2-[(benzyloxy)methyl]piperazine-1-carboxylate → HCID 136121359, compound

HRID 2062156Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1.[CH2:20]([O:27][CH2:28][C@H:29]1[CH2:34][NH:33][CH2:32][CH2:31][N:30]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C(N(CC)CC)C>[CH2:20]([O:27][CH2:28][C@H:29]1[CH2:34][N:33]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[N:3]=2)[CH2:32][CH2:31][N:30]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (450 mg, 1.66 mmol) in 10 mL DMF was added a solution of (R)-tert-butyl 2-((benzyloxy)methyl)piperazine-1-carboxylate (610 mg, 1.99 mmol) in DMF and triethylamine (0.46 mL). The reaction mixture was then refluxed at 85° C. for 30 minutes, quenched with water, extracted twice with CH2Cl2, dried over Na2SO4, and concentrated to give (R)-tert-butyl 2-((benzyloxy)methyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate (760 mg, 85%). This material was used in the next step without further purification. LC/MS: m/z 541.5 (M+H)+ at 3.37 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

customquenched with water
extractionextracted twice with CH2Cl2
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-f700cac9eae44162afef90a67541bdda
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283354B2

Reaction notes

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