Hydrazine hydrate (1:1) → HCID 136928086, compound

HRID 64365Notes

Reaction equation

HRID 64365 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]1[CH2:18][N:17]2[N:19]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)[C:21]([C:22]([NH2:24])=[O:23])=[C:16]2[NH:15][CH2:14]1.O.NN>CO>[NH2:3][CH2:12][CH:13]1[CH2:18][N:17]2[N:19]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)[C:21]([C:22]([NH2:24])=[O:23])=[C:16]2[NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1369280806-((1,3-Dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 136928086HCID 136928086, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-((1,3-dioxoisoindolin-2-yl)methyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide (200 mg, 0.40 mmol) in CH3OH (5 mL) was added hydrazine hydrate (1 mL, 80% of aqueous solution). The mixture was stirred at 70° C. under N2 for 4 hr, concentrated and purified by chromatography column on 5 g of silica gel eluting with DCM/CH3OH to afford 63 mg (43%) of 6-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide as colorless oil. MS (ESI) m/e [M+1]+ 363.9.

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography column on 5 g of silica gel eluting with DCM/CH3OH

Sources & evidence

ORD record
ord-46afa9c29da84fe4ac1f871b9249d57f
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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