1,2-Dichloroethane → HCID 66703689, compound

HRID 426014Notes

Reaction equation

HRID 426014 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:31])[C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=3[NH:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:32].[CH:33]1([CH:36]=O)[CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[Cl:54]CCCl>C(O)(=O)C>[ClH:54].[CH:33]1([CH2:36][N:28]2[CH2:29][CH2:30][CH:25]([NH:24][C:15]3[CH:16]=[C:17]([C:20]([F:22])([F:23])[F:21])[CH:18]=[CH:19][C:14]=3[C:13]([NH:12][C:9]3[CH:10]=[C:11]4[C:6]([CH2:5][CH2:4][C:3](=[O:32])[N:2]4[CH3:1])=[CH:7][CH:8]=3)=[O:31])[CH2:26][CH2:27]2)[CH2:35][CH2:34]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57867990HCID 57867990, compound

Product 1

HCID 66703689HCID 66703689, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After dissolving N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-2-(piperidin-4-ylamino)-4-(trifluoromethyl)benzamide (200 mg), cyclopropanecarbaldehyde (0.10 mL) and acetic acid (0.026 ml) in 1,2-dichloroethane (4 ml), sodium triacetoxyborohydride (285 mg) was added thereto. After stirring at room temperature for 2 hours, 1 M sodium hydroxide aqueous solution was added thereto, followed by extraction with chloroform. After drying the organic layer with sodium sulfate, the solution was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia, 1:0:0 to 90:9:1). By treating the resulting free base with 4 M hydrogen chloride/ethyl acetate, 2-{[1-(cyclopropylmethyl)piperidin-4-yl]amino}-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide hydrochloride (199 mg) was obtained as an amorphous.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform
  3. dry with materialAfter drying the organic layer with sodium sulfate
  4. concentrationthe solution was concentrated under a reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia, 1:0:0 to 90:9:1)
  6. additionBy treating the resulting free base with 4 M hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-3edc473cf9594518a0f224e49d47c1ed
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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