p-Toluenesulfonic acid monohydrate → HCID 66621372, compound

HRID 415317Notes

Reaction equation

HRID 415317 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([CH:31]=[CH:32][CH:33]=3)[C:17]([NH:19][C:20]3[C:21](O)=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25][CH3:26])=[O:24])=[O:18])=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([C:17]4[O:18][C:21]5[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=[CH:29][C:20]=5[N:19]=4)[CH:31]=[CH:32][CH:33]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66621017HCID 66621017, compound

Product 1

HCID 66621372HCID 66621372, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzamido)-2-hydroxybenzoate (160 mg, 0.35 mmol) and 4-methylbenzenesulfonic acid monohydrate (200 mg, 1 mmol) were added to toluene (10 mL) and the mixture was stirred at reflux for 16 hr. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated to yield methyl 2-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)benzo[d]oxazole-7-carboxylate as a solid (130 mg, yield: 85%). LC-MS (ESI) m/z: 434 (M+1)+.

Workup

  1. temperatureat reflux for 16 hr
  2. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-71e2b06ac4db49df9b2c3558a4b89ccb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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