Triethylamine → HCID 136121380, compound

HRID 2062355Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl(S)-pyrrolidin-3-ylcarbamate (245 mg, 1.31 mmol) was dissolved in 1.8 mL of anhydrous CH2Cl2 and cooled to 0° C. 2-(4-Chloro-7-methylquinazolin-2-yl)phenol (300 mg, 1.1 mmol) dissolved in 1.8 mL of anhydrous CH2Cl2 was added dropwise to the mixture followed by triethylamine (134 mg, 184 μL, 1.32 mmol). The reaction was allowed to warm to room temperature and was stirred overnight. Purification via silica gel chromatography using 10-100% ethyl acetate/hexanes gave tert-butyl(S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate. LC/MS: m/z 421.0 (M+H)+ at 2.84 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

additionwas added dropwise to the mixture
temperatureto warm to room temperature
customPurification via silica gel chromatography

Sources & evidence

ORD record: ord-7a11b6dc75bc41209e4642ad0d591197
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283354B2

Reaction notes

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