Sodium Bicarbonate → 3-[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-propionamide

HRID 2101489Notes

Reaction equation

HRID 2101489 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][NH:6][CH2:7][CH2:8][C:9]([NH2:11])=[O:10].[Cl:15][C:16]1[CH:17]=[C:18]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH:25]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][N:6]([CH2:5][C:4]1[CH:12]=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=1)[CH2:7][CH2:8][C:9]([NH2:11])=[O:10]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 431514743-(3-Fluoro-benzylamino)-propionamideHCID 578014901-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 119524873-[[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-propionamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(3-Fluoro-benzylamino)-propionamide (98 mg, 0.5 mmol), 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde, (see Example 2) (102 mg, 0.4 mmol) and CH2Cl2 (2 mL) was added NaBH(OAc)3 (119 mg, 0.56 mmol). The mixture was stirred at ambient temperature for 3 h before addition of saturated NaHCO3 (8 mL). The mixture was extracted with CH2Cl2 (2×15 mL) and the combined CH2Cl2 extracts dried over Na2SO4. Volatiles were removed in vacuo and the residue purified by column chromatography (silica gel, 20:1 CH2Cl2/MeOH) to provide the title compound (71 mg, 40%) as colorless, viscous oil: ESI MS m/z 435 [C21H21Cl2FN4O+H]+.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (2×15 mL)
  2. dry with materialthe combined CH2Cl2 extracts dried over Na2SO4
  3. customVolatiles were removed in vacuo
  4. customthe residue purified by column chromatography (silica gel, 20:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-67a91faa204a4506895bf81ad0b6ef5f
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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