Ammonia → HCID 70364112, compound

HRID 280356Notes

Reaction equation

HRID 280356 reaction equation
C([N:3]=[C:4]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[N:26]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:25]3[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=3[N:23]=2)[CH2:17][CH2:16]1)[NH:5][CH2:6][CH:7](OC)[O:8]C)#N.Cl.N>O>[OH2:8].[NH2:3][C:4]1[N:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21][C:22]3[N:26]([CH2:27][C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:25]4[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=4[N:23]=3)[CH2:17][CH2:16]2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 178495970HCID 178495970, compound

Product 1

HCID 70364112HCID 70364112, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 parts of N"-cyano-N-(2,2-dimethoxyethyl)-N'-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]guanidine and 60 parts of concentrated hydrochloric acid was stirred and refluxed for one hour. Water was added and the whole was alkalized with ammonia. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane, yielding 1 part of N-[1-[2-(2-amino-1H-imidazol-1yl]ethyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine monohydrate; mp. 171.4° C. (compound 60).

Workup

  1. temperaturerefluxed for one hour
  2. extractionThe product was extracted with 4-methyl-2-pentanone
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-0616558610214a768dfaeb4a3bc23e09
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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