Dichloromethane → HCID 68791834, compound

HRID 1161002Notes

Reaction equation

HRID 1161002 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([N:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[NH:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=1.[CH3:38][C:39]([CH3:43])([CH3:42])[CH:40]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl:63]CCl>CO.O>[ClH:63].[ClH:63].[CH2:21]([N:16]([CH2:17][CH:18]([CH3:19])[CH3:20])[C:14]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([NH:25][C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[N:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:38][C:39]([CH3:43])([CH3:42])[CH3:40])[C:9]=2[CH:10]=1)=[O:15])[CH:22]([CH3:24])[CH3:23]

Participants

8

Reactant 5

HCID 6344Dichloromethane2×HCID 12417PivalaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 44432895HCID 44432895, compound

Product 1

HCID 68791834HCID 68791834, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3-aminopropyl)-N,N-diisobutyl-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxamide (100 mg, 1 eq) and trimethylacetaldehyde (25 mg, 1.5 eq) in dichloromethane (1 ml) is stirred for 4 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (1 ml) then sodium triacetoxyborohydride is added (41 mg, 2 eq). After 1 hour at a temperature of approximately 20° C., dichloromethane (20 ml) and water saturated with sodium hydrogen carbonate (10 ml) are added to the mixture. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1) produces the expected compound in the form of a base. The corresponding hydrochloride salt is formed by adding a 1N solution of hydrochloric acid in ether. The precipitate obtained is filtered and dried in order to produce the expected dihydrochloride compound (83 mg, 65% yield).

Workup

  1. extractionAfter decantation and extractions
  2. washthe combined organic phases are washed with salt water
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated under reduced pressure at 40° C
  5. customPurification of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-5cea5a9d74cd43f5a33a059a645722ac
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

Loading…