Water → HCID 66603938, compound

HRID 71116Notes

Reaction equation

HRID 71116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:32][NH2:33])[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[O:28][C:27]([CH3:29])=[N:26][CH:25]=5)=[C:20]([O:30][CH3:31])[CH:19]=4)=[N:16][N:17]=[C:10]23)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:41](OC(=O)C)(=[O:43])[CH3:42].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:32][NH:33][C:41](=[O:43])[CH3:42])[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[O:28][C:27]([CH3:29])=[N:26][CH:25]=5)=[C:20]([O:30][CH3:31])[CH:19]=4)=[N:16][N:17]=[C:10]23)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 666040871-{8-(3,4-Dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methanamine

Product 1

HCID 66603938HCID 66603938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-{8-(3,4-dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methanamine (76.7 mg) and triethylamine (26.2 μL) in THF (1 mL) was added acetic anhydride under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (59.6 mg).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe solid was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-2b95e2318e7e4b4b8a5c78433ef20b5a
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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