Cyclohexylamine → HCID 59703555, compound

HRID 556457Notes

Reaction equation

HRID 556457 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:20]([CH2:27][C:28]([OH:30])=O)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:27][C:28]([NH:37][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24951233HCID 24951233, compound

Product 1

HCID 59703555HCID 59703555, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-phenyl-amino}-acetic acid (70 mg, 0.159 mmol), cyclohexylamine (19 mg, 0.191 mmol) EDC.HCl (36 mg, 0.191 mmol), HOBt (26 mmg, 0.191 mmol) and DIPEA (25 mg, 0.191 mmol) in acetonitrile (3 mL) was stirred at room temperature for overnight. The reaction mixture was concentrated and the residue was purified with chromatography to give 45 mg of rac-2-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-phenyl-amino}-N-cyclohexy-acetamide as a yellow solid. MS m/z 522 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified with chromatography

Sources & evidence

ORD record
ord-f090c30c04974ee58b4b7539013afd56
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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