Thiophene → HCID 13588201, compound

HRID 1493920Notes

Reaction equation

HRID 1493920 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]3[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:21]4[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=4[N:19]=3)[CH2:13][CH2:12]2)[C:3]=1[NH2:35].S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>C(O)C.[Pd].CO>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:22]2[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=[C:18]2[NH:17][CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:4]3[C:3]([NH2:35])=[CH:2][N:7]=[CH:6][N:5]=3)[CH2:12][CH2:13]2)=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 13588146HCID 13588146, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13588201HCID 13588201, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1.5 parts of 6-chloro-N4 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4,5-pyrimidinediamine, 3 parts of a solution of thiophene in ethanol 4%, 1 part of potassium acetate and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 1 part of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The solid residue was taken up in water. The solution was treated with ammonia. The product was extracted with trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from a mixture of 4-methyl-2-pentanone, yielding 1 part (72.4%) of N4 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4,5-pyrimidinediamine; mp. 207.7° C. (intermediate 165).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe solution was treated with ammonia
  4. extractionThe product was extracted with trichloromethane
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from a mixture of 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-500dd0595685439d9dba3b33e9a14417
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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