Sodium Bicarbonate → HCID 178521354, compound

HRID 2225223Notes

Reaction equation

HRID 2225223 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:25])[CH2:11][NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:5][CH2:4]1.O[C:27]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(Cl)Cl>[O:25]=[C:10]([NH:9][C@H:6]1[CH2:5][CH2:4][C@@H:3]([NH:2][CH:37]2[CH2:38][CH2:39][C:34]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:35][CH2:36]2)[CH2:8][CH2:7]1)[CH2:11][NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5837414-Hydroxy-4-phenylcyclohexan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 178479272HCID 178479272, compound

Product 1

HCID 178521354HCID 178521354, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

N-(2-(cis-4-Amino-cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (120 mg, 0.315 mmol, 1 eq), 4-hydroxy-4-phenylcyclohexanone (60 mg, 0.315 mmol, 1 eq) and sodium triacetoxyborohydride (134 mg, 0.631 mmol, 2 eq) were stirred in 2% acetic acid/methylene chloride (10 mL) at room temperature for 20 hours. Worked up by adding saturated sodium bicarbonate (10 mL). Stirred 10 minutes then extracted 3 times with methylene chloride (10 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 100% ethyl acetate to 4:1 methylene chloride/methanol to give N-(2-oxo-2-(cis-4-(4-phenylcyclohex-3-enylamino)cyclohexylamino)ethyl)-3-(trifluoromethyl)benzamide (10 mg) as a tan solid. MS found: (M+H)+=500.33.

Workup

  1. extractionthen extracted 3 times with methylene chloride (10 mL)
  2. dry with materialdried (sodium sulfate)
  3. customto give an oil
  4. customPurified over silica gel in 100% ethyl acetate to 4:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-daddb7627d084878b9ba51f8e2a99a81
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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