Carbon Disulfide → 9-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-9H-purin-8-amine

HRID 256675Notes

Reaction equation

HRID 256675 reaction equation
[C:1](=[S:3])=S.[NH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:15]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:16]3[C:21]([N:22]=2)=[CH:20][N:19]=[CH:18][N:17]=3)[CH2:9][CH2:8]1>O1CCCC1>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:15]2[C:14]([NH:13][CH:10]3[CH2:11][CH2:12][N:7]([CH2:6][CH2:5][N:4]=[C:1]=[S:3])[CH2:8][CH2:9]3)=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][CH:20]=3)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 19785318N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine

Product 1

HCID 197852259-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-9H-purin-8-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (-10° C.) mixture of 5.6 parts of N,N'-methanetetraylbis[cyclohexanamine], 13.9 parts of carbon disulfide and 90 parts of tetrahydrofuran were added portionwise 10 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine. Upon completion, the temperature was allowed to rise to room temperature and the reaction mixture was evaporated, yielding 16 parts of 9-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-9H-purin-8-amine (compound 181).

Workup

  1. temperaturecooled
  2. customto rise to room temperature
  3. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-1fec5526cad443858fa95e8c34d84e52
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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