2-Butanamine, 2-methyl- → 3-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(1,1-dimethylpropyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one

HRID 1081501Notes

Reaction equation

HRID 1081501 reaction equation
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].[CH3:34][C:35]([NH2:39])([CH3:38])[CH2:36][CH3:37].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:11]1([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:33]=[CH:32][C:7]=3[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:28])[NH:39][C:35]([CH3:38])([CH3:34])[CH2:36][CH3:37])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9]2=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 689862-Butanamine, 2-methyl-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

Product 1

HCID 233642733-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(1,1-dimethylpropyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.09 g of the compound obtained in EXAMPLE 13, 1 ml of 1,1-dimethylpropylamine, 1.2 g of BOP, 1 ml of DIPEA and 20 ml of DCM is stirred for 2 hours at RT. The reaction mixture is evaporated under vacuum, the residue is extracted with AcOEt, washed with a 1N solution of HCl, with a 1N solution of NaOH and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (99/1; v/v) as the eluent to give 0.88 g of the expected product in the form of white crystals. M.p.=219° C.

Workup

  1. customThe reaction mixture is evaporated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with a 1N solution of HCl, with a 1N solution of NaOH and with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (99/1; v/v) as the eluent

Sources & evidence

ORD record
ord-1a70902aca5941988f78041b3fc8cba6
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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