Calciumoxide → HCID 88502046, compound

HRID 845795Notes

Reaction equation

HRID 845795 reaction equation
Cl.Cl.Cl[C:4]1[N:9]=[C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]3[N:24]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:23]4[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=4[N:21]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:6][N:5]=1.[O-2:37].[Ca+2].[H][H]>[Pd].CO>[OH2:37].[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:24]2[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]=[C:20]2[NH:19][CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][NH:10][C:8]3[CH:7]=[CH:6][N:5]=[CH:4][N:9]=3)[CH2:14][CH2:15]2)=[CH:31][CH:30]=1.[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:24]2[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]=[C:20]2[NH:19][CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][NH:10][C:8]3[CH:7]=[CH:6][N:5]=[CH:4][N:9]=3)[CH2:14][CH2:15]2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 6850728CalciumoxideHCID 19907866HCID 19907866, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 88502046HCID 88502046, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.2 parts of N-[1-[2-[(2-chloro-4-pyrimidinyl)amino]ethyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine dihydrochloride, 3 parts of calcium oxide and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 20%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.1 parts of 1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-pyrimidinylamino)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine hemihydrate; mp. 133.9° C. (compound 94).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-24d303ed4b2d45d484325aee6d402a25
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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