Urea → HCID 13983129, compound

HRID 893700Notes

Reaction equation

HRID 893700 reaction equation
[Cl:1][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].N[C:37](N)=[O:38]>O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[NH:35][C:37](=[O:38])[N:8]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 1176UreaHCID 13588146HCID 13588146, compound

Product 1

HCID 13983129HCID 13983129, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.5 Parts of 6-chloro-N4 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-4,5-pyrimidinediamine and 3.6 parts of urea were heated together till about 220° C. during 10 minutes. The resulting melt was cooled and suspended in water. The solid was filtered off, washed with water and ethanol and recrystallized from a mixture of N,N-dimethylacetamide, ethanol and water, yielding 3.9 parts (49.9%) of 6-chloro-9-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-7.9-dihydro-8H-purin-8-one; mp. 266.2° C. (compound 144).

Workup

  1. temperatureThe resulting melt was cooled
  2. filtrationThe solid was filtered off
  3. washwashed with water and ethanol
  4. customrecrystallized from a mixture of N,N-dimethylacetamide, ethanol and water

Sources & evidence

ORD record
ord-7ef4e83a5a5e465394940a5d39b6fc90
Source dataset
uspto-grants-1992_06
Patent number
US05126339

Reaction notes

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