1,1-Dichloroethane → HCID 11526247, compound

HRID 553174Notes

Reaction equation

HRID 553174 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-bc89a0c8bb374d9d899db28507451f33
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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