Cyclohexylamine → Rac-6-chloro-3-(3-chloro-benzyl)-3-cyclohexylamino-1,3-dihydro-indol-2-one

HRID 556449

Reaction equation

HRID 556449 reaction equation
Br[C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>O>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)([NH:27][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:3](=[O:12])[NH:4]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 24950915Rac-6-chloro-3-(3-chloro-benzyl)-3-cyclohexylamino-1,3-dihydro-indol-2-oneYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.27 mmol) (from example 1c supra), cyclohexylamine (40 mg, 0.41 mmol) and DIPEA (104.5 mg, 0.81 mmol) in dimethyl formide (2 mL) was stirred at room temperature for 2 h. Then water (10 mL) was added and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic layer was concentrated and the residue was purified by preparative HPLC to give 51 mg of rac-6-chloro-3-(3-chloro-benzyl)-3-cyclohexylamino-1,3-dihydro-indol-2-one as a white solid. MS: 389 (M+H)+.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  2. concentrationThe combined organic layer was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2d1e6a938619493e979038dbeb924010
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Linked notes

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