Acetic Acid → HCID 11855483, compound

HRID 900690Notes

Reaction equation

HRID 900690 reaction equation
C=O.[C:3](O)(=O)C.[Cl:7][C:8]1[C:9]([N:34]2[CH2:39][CH2:38][CH:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:36][CH2:35]2)=[N:10][CH:11]=[C:12]([C:14](=[O:33])[NH:15][C:16]2[S:17][C:18]([CH2:27][NH:28][CH:29]3[CH2:32][CH2:31][CH2:30]3)=[C:19]([C:21]3[S:22][CH:23]=[C:24]([Cl:26])[CH:25]=3)[N:20]=2)[CH:13]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl.ClCCCl>[Cl:7][C:8]1[C:9]([N:34]2[CH2:39][CH2:38][CH:37]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:36][CH2:35]2)=[N:10][CH:11]=[C:12]([C:14](=[O:33])[NH:15][C:16]2[S:17][C:18]([CH2:27][N:28]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[CH3:3])=[C:19]([C:21]3[S:22][CH:23]=[C:24]([Cl:26])[CH:25]=3)[N:20]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23117177HCID 23117177, compound

Product 1

HCID 11855483HCID 11855483, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

110 μl of a formaldehyde aqueous solution (35%) and 76 μl of acetic acid were added to 2 ml of 1.2-dichloroethane solution of 79 mg of ethyl 1-[3-chloro-5-({4-(4-chlorothiophen-2-yl)-5-[(cyclobutylamino)methyl]thiazol-2-yl}carbamoyl)-2-pyridyl]piperidine-4-carboxylate, and the mixture was stirred at room temperature for 1 hour. Subsequently, 45 mg of NaBH(OAc)3 was added, and the solution was stirred at room temperature for 1 hour. Chloroform was added to the reaction solution, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution, with water and with brine, and then dried over sodium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (hexane:EtOAc=4:1 to 2:1) to obtain 58 mg of ethyl 1-{3-chloro-5-[(4-(4-chlorothiophen-2-yl)-5-{[cyclobutyl(methyl)amino]methyl}thiazol-2-yl)carbamoyl]-2-pyridyl}piperidine-4-carboxylate.

Workup

  1. stirringthe solution was stirred at room temperature for 1 hour
  2. washthe organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution, with water and with brine
  3. dry with materialdried over sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (hexane:EtOAc=4:1 to 2:1)

Sources & evidence

ORD record
ord-4f390d635173473e9780d7169cfc6d39
Source dataset
uspto-grants-2008_04
Patent number
US07361658B2

Reaction notes

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