1-Methyl-2-nitro-1-nitrosoguanidine → N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N'-nitroguanidine

HRID 280343

반응식

HRID 280343 반응식
[CH3:1][N:2](N=O)/[C:3](/[NH2:8])=[N:4]/[N+:5]([O-:7])=[O:6].NC[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[N:25]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:24]3[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=3[N:22]=2)[CH2:16][CH2:15]1>C(O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][N:25]2[C:24]3[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=3[N:22]=[C:21]2[NH:20][CH:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:1][NH:2][C:3]([NH:4][N+:5]([O-:7])=[O:6])=[NH:8])[CH2:19][CH2:18]2)=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 95620601-Methyl-2-nitro-1-nitrosoguanidineHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

생성물 1

HCID 178512207N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N'-nitroguanidine수율 33%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1.5 parts of N-methyl-N'-nitro-N-nitrosoquanidine, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine and 80 parts of ethanol 50% was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried overnight at 110° C., yielding 1.5 parts (33%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-N'-nitroguanidine; mp. 146.7° C. (compound 23).

후처리

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 2-propanol
  7. filtrationThe product was filtered off
  8. customdried overnight at 110° C.

출처 및 근거

ORD 기록
ord-47ecba52425048cd89518303a7e74ba9
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588722

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