Water → 1-Hydroxybenzotriazole hydrate

HRID 1929738Notes

Reaction equation

HRID 1929738 reaction equation
C(C1C=[N:6][N:7]2[C:12](C3C=CC(Cl)=CC=3)=[C:11]([C:20]3C=CC=C[C:21]=3Cl)C=NC=12)(O)=[O:2].[OH2:27].C([N:30]([CH2:33][CH3:34])CC)C>C(Cl)(Cl)Cl>[OH2:2].[OH:27][N:30]1[C:33]2[CH:34]=[CH:21][CH:20]=[CH:11][C:12]=2[N:7]=[N:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 67272265HCID 67272265, compound

Product 1

HCID 27960291-Hydroxybenzotriazole hydrate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-carboxy-6-(2-chlorophenyl)-7-(4-chlorophenyl)-pyrazolo[1,5-a]pyrimidine (compound obtained in Reference Example 1(4), 165 mg) in chloroform (1.0 mL containing amylene) was added the compound obtained in Reference Example 13(2), water-soluble carbodiimide HCl (123 mg), 1-hydroxybenzotriazole monohydrate (97 mg), and triethylamine (178 μL) and the mixture was stirred at room temperature overnight. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution (2 mL) and the mixture was stirred and extracted with chloroform. The extract was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=90/10 to 70/30) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-[N-(4-tetrahydrothiopyranyl)carbamoyl]pyrazolo[1,5-a]pyrimidine (50 mg; yield: 24%) as a pale yellow powder.

Sources & evidence

ORD record
ord-504525f0191f46d6b1368b395dd69347
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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