Water → HCID 11247457, compound

HRID 403050Notes

Reaction equation

HRID 403050 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:12]([NH:14][CH:15]2[CH2:17][CH2:16]2)=[O:13])=[O:7])=[CH:4][CH:3]=1.Br[CH2:25][C:26]1[N:31]=[C:30]([CH2:32][OH:33])[CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:15]1([NH:14][C:12](=[O:13])[C:11]2[CH:18]=[CH:19][C:20]([CH3:21])=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([O:1][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[C:30]([CH2:32][OH:33])[N:31]=4)=[CH:23][CH:22]=3)[CH:10]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10878213[6-(Bromomethyl)pyridin-2-yl]methanolHCID 66631169N-cyclopropyl-3-[(4-hydroxybenzoyl)amino]-4-methylbenzamide

Product 1

HCID 11247457HCID 11247457, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-{[4-(hydroxy)benzoyl]amino}-N-cyclopropyl-4-methylbenzamide (100 mg, 0.323 mmol), [6-(bromomethyl)pyridin-2-yl]methanol (71 mg, 0.355 mmol) and potassium carbonate (49 mg, 0.355 mmol) were mixed in acetonitrile (3 mL) and the reaction was stirred at room temperature for 16 h. The reaction was then heated at 100° C. in the microwave for 10 mins. Water (10 mL) was added and the mixture was extracted with DCM (3×15 mL). The organic layers were combined and evaporated to give a white solid which was triturated with DCM to give the title compound as a white solid (80 mg, 58%); NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.68 (m, 2H), 2.25 (s, 3H), 2.85 (m, 1H), 4.59 (s, 2H), 5.24 (s, 2H), 7.16 (d, 2H), 7.32 (d, 1H), 7.38 (d, 1H), 7.45 (d, 1H), 7.63 (m, 1H), 7.80 (m, 2H), 7.97 (d, 2H), 8.36 (d, 1H), 9.82 (s, 1H); Mass Spectrum: M+H+ 432.

Workup

  1. temperatureThe reaction was then heated at 100° C. in the microwave for 10 mins
  2. extractionthe mixture was extracted with DCM (3×15 mL)
  3. customevaporated
  4. customto give a white solid which
  5. customwas triturated with DCM

Sources & evidence

ORD record
ord-76c03a0446254cedacc7d4e51c93bd40
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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