Ammonia → HCID 178519830, compound

HRID 2294918Notes

Reaction equation

HRID 2294918 reaction equation
[N:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:30]1[CH:35]=[C:34]([C:36](Cl)=[O:37])[CH:33]=[N:32][CH:31]=1.N>ClCCl>[N:30]1[CH:35]=[C:34]([C:36]([N:4]2[CH2:3][CH2:2][N:1]([C@H:7]3[CH2:12][CH2:11][C@H:10]([N:13]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[NH:15][C:14]4=[O:22])[CH2:9][CH2:8]3)[CH2:6][CH2:5]2)=[O:37])[CH:33]=[N:32][CH:31]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 15839553Pyrimidine-5-carbonyl chlorideHCID 178518598HCID 178518598, compound

Product 1

HCID 178519830HCID 178519830, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.044 g of 1,3-dihydro-1-{trans-4-[1-piperazinyl]-1-cyclohexyl}-2H-benzimidazol-2-one and 0.2 mL of triethylamine in 3 mL of dichloromethane was added 0.030 g of pyrimidine-5-carboxylic acid chloride. After 2 h, 5 mL of dilute aqueous ammonia was added and the mixture stirred for an additional 30 min. The organic layer was separated, the aqueous layer extracted with two additional 20 mL portions of chloroform and the combined organic extracts dried over MgSO4 and concentrated under reduced pressure. Chromatography over silica gel eluting with 10% methanol in ethyl acetate gave 0.030 g of 1,3-dihydro-1-{trans-4-[4-(5-pyrimidinecarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 9.76 (s, 1H), 9.29 (s, 1H), 8.83 (s, 2H), 7.16-7.04 (m, 4H), 4.27 (m, 1H), 3.84 (s, 2H), 3.48 (s, 2H), 2.72 (s, 2H), 2.61 (s, 2H), 2.56 (m, 1H), 2.30 (q, 2H), 2.05 (m, 4H), 1.86 (br s, 1H), 1.5 (q, 2H). The dihydrochloride salt was precipitated from chloroform/ethyl acetate: Analysis calculated for C22H26N6O2.2HCl.0.65 CHCl3C: 48.84, H: 5.18, N: 15.09 found C: 48.85, H: 5.36, N: 14.72.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with two additional 20 mL portions of chloroform
  3. dry with materialthe combined organic extracts dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41fe15e6e5584f89861f08cf89d41249
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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