Hydrochloric Acid → HCID 136121418, compound

HRID 2062358Notes

Reaction equation

HRID 2062358 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.[NH:20]1[CH2:23][CH:22]([C:24]([OH:26])=[O:25])[CH2:21]1.C(N(CC)CC)C.Cl>CN(C=O)C.O>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:4]1[N:3]=[C:2]([N:20]2[CH2:23][CH:22]([C:24]([OH:26])=[O:25])[CH2:21]2)[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 931923-azetidinecarboxylic AcidHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136121418HCID 136121418, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (2.84 g, 10.5 mmol) and azetidine-3-carboxylic acid (1.06 g, 10.5 mmol) in DMF (100 mL) was added triethylamine (3.18 g, 4.39 mL, 31.5 mmol). The reaction was stirred at room temperature overnight then diluted with H2O (400 mL). The pH of the solution was adjusted to 3-4 by addition of an aqueous 1 M HCl solution. The white precipitate then obtained was filtered, washed with H2O, and purified by silica gel chromatography using 0-15% MeOH—CH2Cl2 giving 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)azetidine-3-carboxylic acid. LC/MS: m/z 336.3 (M+H)+ at 1.97 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe white precipitate then obtained
  2. filtrationwas filtered
  3. washwashed with H2O
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a5466801d7834fd2a5acbaed8dbf4965
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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