Water → HCID 15037452, compound

HRID 704734Notes

Reaction equation

HRID 704734 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([CH2:9][N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=[C:11]2[NH:19][CH:20]2[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][OH:29])[CH2:22][CH2:21]2)=[CH:6][CH:5]=1.Cl[C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1.O>CN(C)C=O>[N:32]1[CH:33]=[CH:34][CH:35]=[N:36][C:31]=1[O:29][CH2:28][CH2:27][N:23]1[CH2:24][CH2:25][CH2:26][CH:20]([NH:19][C:11]2[N:10]([CH2:9][C:7]3[O:8][C:4]([CH3:3])=[CH:5][CH:6]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=2)[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 15037451HCID 15037451, compound

Product 1

HCID 15037452HCID 15037452, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 1 part of a sodium hydride dispersion 50% and 94 parts of N,N-dimethylformamide is added dropwise a solution of 5.5 parts of hexahydro-4-[[3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]-pyridin-2-yl]amino]-1H-azepine-1-ethanol in N,N-dimethylformamide. Upon complete addition, stirring is continued for 15 minutes at room temperature. 1.9 Parts of 2-chloropyrimidine are added portionwise and upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is decomposed with water and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent was evaporated. The residue is converted into the ethanedioate salt in ethanol. The salt is filtered off and dried, yielding 3.4 parts (34.8%) of N-[hexahydro-1-[2-(2-pyrimidinyloxy)ethyl]-1H-azepin-4-yl]-3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine (compound 169).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. waitis continued for 2 hours at room temperature
  4. extractionthe product is extracted with dichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent was evaporated
  12. filtrationThe salt is filtered off
  13. customdried

Sources & evidence

ORD record
ord-f924288cee004e8db98cf08d52c6e2be
Source dataset
uspto-grants-1991_01
Patent number
US04988689

Reaction notes

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