1-Hydroxybenzotriazole → HCID 131733106, compound

HRID 1520301Notes

Reaction equation

HRID 1520301 reaction equation
[CH3:1][CH:2]([CH3:30])[CH:3]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19].[NH:31]1[CH2:36][CH2:35][CH2:34][C@@H:33]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:32]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.O.CN(C=O)C>[CH3:1][CH:2]([CH3:30])[CH:3]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([N:31]2[CH2:36][CH2:35][CH2:34][C@@H:33]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:32]2)=[O:26])=[CH:28][CH:29]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117840315HCID 117840315, compound

Product 1

HCID 131733106HCID 131733106, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-((2-methyl-1-(2-methyl-4-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenyl)propyl)amino)benzoic acid obtained in step C, ethyl (3R)-piperidine-3-carboxylate (0.106 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (132 mg), 1-hydroxybenzotriazole (93 mg), N,N-diisopropylethylamine (0.180 mL), 4-dimethylaminopyridine (4.2 mg) and DMF (0.860 mL) was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (152.3 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b93d09049a6c46aa8db760192d7511d3
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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