1,1-Dichloroethane → HCID 66703671, compound

HRID 426016Notes

Reaction equation

HRID 426016 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15]C(Cl)C.[NH2:19][C@H:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]1[NH:26][C:27]1[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[CH:44][C:28]=1[C:29]([NH:31][C:32]1[CH:40]=[C:39]2[C:35]([C:36]([CH3:43])([CH3:42])[C:37](=[O:41])[NH:38]2)=[CH:34][CH:33]=1)=[O:30].[C:52]1(=O)[CH2:56][CH2:55][CH2:54][CH2:53]1.[OH-].[Na+]>C(O)(=O)C>[ClH:15].[CH:52]1([NH:19][C@H:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]2[NH:26][C:27]2[CH:47]=[C:46]([C:48]([F:51])([F:49])[F:50])[CH:45]=[CH:44][C:28]=2[C:29]([NH:31][C:32]2[CH:40]=[C:39]3[C:35]([C:36]([CH3:43])([CH3:42])[C:37](=[O:41])[NH:38]3)=[CH:34][CH:33]=2)=[O:30])[CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

7

Reactant 5

HCID 63651,1-DichloroethaneHCID 8452Cyclopentanone2×HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 57867992HCID 57867992, compound

Product 1

HCID 66703671HCID 66703671, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Sodium triacetoxyborohydride (138 mg) was added to a dichloroethane (20 mL) solution of 2-{[(1S,2S)-2-aminocyclohexyl]amino}-N-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-4-(trifluoromethyl)benzamide (200 mg), cyclopentanone (40 mg) and acetic acid (29 mg), followed by stirring at room temperature for 1 day. Acetic acid (260 mg), cyclopentanone (140 mg) and sodium triacetoxyborohydride (140 mg) were added to the reaction liquid, followed by stirring for 1 day. A 1 M sodium hydroxide aqueous solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol, 1:0 to 85:15). By treating the resulting free base with 4 M hydrogen chloride/ethyl acetate, 2-{[(1S,2S)-2-(cyclopentylamino)cyclohexyl]amino}-N-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-4-(trifluoromethyl)benzamide hydrochloride (53 mg) was obtained as a white solid.

Workup

  1. stirringby stirring for 1 day
  2. extractionfollowed by extraction with chloroform
  3. concentrationThe organic layer was concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol, 1:0 to 85:15)
  5. additionBy treating the resulting free base with 4 M hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-258dd6371ae44935b8116520179543f9
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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