HCID 66980248, compound → HCID 86699860, compound

HRID 1423315Notes

Reaction equation

HRID 1423315 reaction equation
O=[C:2]1[CH:10]([C:11]#[N:12])[CH2:9][CH2:8][C:3]21[S:7][CH2:6][CH2:5][S:4]2.[C:13]1([C:19]2[N:24]=[CH:23][C:22]([C:25]3[CH:26]=[N:27][NH:28][C:29]=3[NH2:30])=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[C:13]1([C:19]2[N:24]=[CH:23][C:22]([C:25]3[CH:26]=[N:27][N:28]4[C:11]([NH2:12])=[C:10]5[CH2:9][CH2:8][C:3]6([S:7][CH2:6][CH2:5][S:4]6)[C:2]5=[N:30][C:29]=34)=[CH:21][CH:20]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 66980248HCID 66980248, compoundHCID 86699859HCID 86699859, compound

Product 1

HCID 86699860HCID 86699860, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 6-oxo-1,4-dithiaspiro[4.4]nonane-7-carbonitrile (485 mg, 2.27 mmol) and 4-(6-phenylpyridin-3-yl)-1H-pyrazol-5-amine (537 mg, 2.27 mmol) in toluene (10 mL) was heated at 115° C. overnight. Concentration afforded crude 3-(6-phenylpyridin-3-yl)-6,7-dihydrospiro[cyclopenta[d]pyrazolo[1,5-a]pyrimidine-5,2′-[1,3]dithiolan]-8-amine, which was converted to 8-amino-3-(6-phenylpyridin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-5-one applying Stork's procedure (G. Stork, K. Zhao, Tetrahedron Letter, 1989, 30, 287) by treating with PhI(OCF3)2. LCMS tR=1.07 Min (5 min run, UV254nm), Mass calculated for, M+341.1, observed LC/MS m/z 342.1 (M+H).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-dd41f3f44a22461084b25f29ae30504b
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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