1,1-Dichloroethane → HCID 11526247, compound

HRID 1714366Notes

Reaction equation

HRID 1714366 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:30])[CH:14]([NH:18][C:19](=[O:29])[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=3)[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]2)[CH2:3][CH2:2]1.ClC(Cl)C.[CH3:35][C:36]([CH3:41])([CH3:40])[CH2:37][CH:38]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(N(CC)CC)C.C1COCC1>[CH3:35][C:36]([CH3:41])([CH3:40])[CH2:37][CH2:38][N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:30])[CH:14]([NH:18][C:19](=[O:29])[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=3)[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 11517334HCID 11517334, compound

Product 1

HCID 11526247HCID 11526247, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid (1-piperidin-4-yl-1H-imidazol-4-yl)-amide (100 mg, 2.4 mmol) was charged with 1 mL of THF, 1 mL of Dichloroethane, 0.06 mL of triethyamine, 0.03 mL of 3,3-dimethylbutyraldehyde, and 63 mg of sodiumtriacetoxyborohydride. The reaction was stirred overnight, quenched with sodiumbicarbonate, extracted with methylene chloride, and the resultant oil purified by silica gel chromatography to afford the title compound: C13 NMR (100 MHz, CDCl3) 13.9, 18.8, 29.7, 29.9, 33.3, 36.0, 40.9, 43.1, 52.9, 53.1, 54.5, 55.9, 102.8, 103.1, 105.9, 112.3, 112.4, 112.5, 112.6, 131.5, 137.6, 169.2; MS 504.3 m/z (M+1)

Workup

  1. customquenched with sodiumbicarbonate
  2. extractionextracted with methylene chloride
  3. customthe resultant oil purified by silica gel chromatography

Sources & evidence

ORD record
ord-e54a6d54206c442ab180f2d6c8007e6b
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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