Triethylamine → HCID 136121447, compound

HRID 2062299Notes

Reaction equation

HRID 2062299 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][CH2:11][CH2:12][O:13][CH3:14])[CH2:2]1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=2)[N:20]=[C:19]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=2[OH:35])[N:18]=1.C(N(CC)CC)C>C(Cl)Cl>[F:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([OH:35])[C:28]=1[C:19]1[N:18]=[C:17]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][CH2:11][CH2:12][O:13][CH3:14])[CH2:2]2)[C:26]2[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=2)[N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58010683HCID 58010683, compoundHCID 1361213752-(4-Chloro-7-methylquinazolin-2-yl)-3-fluorophenol

Product 1

HCID 136121447HCID 136121447, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxyethyl ((R)-piperidin-3-yl)methylcarbamate (0.24 g, 1.1 mmol) and 2-(4-chloro-7-methylquinazolin-2-yl)-3-fluorophenol (250 mg, 0.865 mmol) in CH2Cl2 was added triethylamine (2.41 mL, 1.73 mmol). After stirring the reaction at room temperature for 2 h, it was quenched with water and then extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 0%-10% EtOAc in CH2Cl2 yielded 2-methoxyethyl ((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (357 mg, 88%). LC/MS: m/z 469.5 (M+H)+ at 2.30 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe reaction at room temperature for 2 h
  2. customit was quenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-d9f03b6cdce94d4c9cb7475eba76d2f9
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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