Sodium Carbonate → HCID 178518595, compound

HRID 2294929Notes

Reaction equation

HRID 2294929 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[NH2:24][C:25]1[CH:26]=[N:27][CH:28]=[N:29][CH:30]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCCl>[NH4+:8].[OH-:1].[N:27]1[CH:26]=[C:25]([NH:24][C@H:2]2[CH2:7][CH2:6][C@H:5]([N:8]3[CH2:13][CH2:12][CH:11]([N:14]4[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[NH:16][C:15]4=[O:23])[CH2:10][CH2:9]3)[CH2:4][CH2:3]2)[CH:30]=[N:29][CH:28]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 344373Pyrimidin-5-amineHCID 5049666Sodium triacetoxyborohydrideHCID 97968491,3-dihydro-1-{1-[4-oxocyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one

Product 2

HCID 14923Ammonium HydroxideHCID 178518595HCID 178518595, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 0.25 g of 1,3-dihydro-1-{1-[4-oxocyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one, 0.25 g of 5-aminopyrimidine (H. Bredereck, F. Effenberger and E. H. Schweizer, Chem. Ber. 1962 95, 803-9), 2 mL of 1,2-dichloroethane, 0.5 mL of acetic acid and 0.35 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was poured into 200 mL chloroform and 20 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of CHCl3 and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. Preparative TLC on silica gel, eluting with 85:15:5 Et2O:MeOH:conc. NH4OH gave 85 mg of trans-1,3-dihydro-1-{1-[1-(5-pyrimidinylamino)cyclohex-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one: 1H NMR (400 MHz, CDCl3 +5% CD3OD) 8.44 (s, 1H), 8.12 (m, 2H), 7.36 (m, 1H), 7.09 (m, 3H), 4.3 (br m, 1H), 3.65 (br m, 2H), 3.2 (br m, 2H), 2.45 (m, 5H), 2.0 (m, 2H), 1.85 (br m, 4H), 1.65 (m, 4H): Analysis calculated for C22H28N6 O.1.05 H2O.0.25 CHCl3 : C: 60.56, H: 7.17, N: 18.68; found C: 60.81, H: 7.17, N: 18.68, and 75 mg of cis-1,3-dihydro-1-{1-[1-(5-pyrimidinylamino)cyclohex-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one: 1H NMR (400 MHz, CDCl3 +5% CD3OD) 8.43 (s, 1H), 8.08 (m, 2H), 7.65 (m, 1H), 7.1 (m, 3H), 4.6 (br m, 1H), 3.6 (br m, 2H), 3.25 (br m, 2H), 3.0 (br m, 5H), 2.3 (m, 4H), 2.0 (m, 2H), 1.75 (br m, 2H), 1.35 (m, 2H): Analysis calculated for C22H28 N6O.0.25 H2O.0.75 CHCl3 : C: 55.90, H: 5.97, N: 17.16; found C: 56.19, H: 5.96, N: 17.14.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of CHCl3
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washPreparative TLC on silica gel, eluting with 85:15:5 Et2O

Sources & evidence

ORD record
ord-3efbe1d4c4d1490e850618c5423df07e
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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