Benzoic acid, 2-isothiocyanato-, methyl ester → 3-[2-[4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl]ethyl]-1,2-dihydro-2-thioxo-4(3H)-quinazolinone

HRID 477691Notes

Reaction equation

HRID 477691 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:14]3[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=3[N:12]=2)[CH2:6][CH2:5]1.[N:28]([C:31]1[CH:40]=[CH:39][CH:38]=[CH:37][C:32]=1[C:33](OC)=[O:34])=[C:29]=[S:30]>O1CCCC1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:15]2[C:14]3[CH:24]=[CH:25][CH:26]=[CH:27][C:13]=3[N:12]=[C:11]2[NH:10][CH:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][N:1]3[C:33](=[O:34])[C:32]4[C:31](=[CH:40][CH:39]=[CH:38][CH:37]=4)[NH:28][C:29]3=[S:30])[CH2:5][CH2:6]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 85243Benzoic acid, 2-isothiocyanato-, methyl esterHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

Product 1

HCID 139831193-[2-[4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl]ethyl]-1,2-dihydro-2-thioxo-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 10.9 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine in 150 parts of tetrahydrofuran was added dropwise a solution of 6 parts of methyl 2-isothiocyanatobenzoate in 30 parts of tetrahydrofuran at room temperature: slightly exothermic reaction, the temperature rose to 30° C. Upon completion, stirring at room temperature was continued for one hour. The reaction mixture was evaporated. The residue was stirred in trichloromethane. The formed precipitate was filtered off and crystallized from 2 -propanone. The product was filtered off and dried, yielding 5.2 parts of 3-[2-[4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl]ethyl]-1,2-dihydro-2-thioxo-4(3H)-quinazolinone; mp. 198.5° C. (compound 131)

Workup

  1. customslightly exothermic reaction
  2. customrose to 30° C
  3. customThe reaction mixture was evaporated
  4. stirringThe residue was stirred in trichloromethane
  5. filtrationThe formed precipitate was filtered off
  6. customcrystallized from 2 -propanone
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-252419c4e93a45c6b2e4013b1658e279
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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