Water → HCID 59536420, compound

HRID 445342Notes

Reaction equation

HRID 445342 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[F:15][C:16]([F:46])([F:45])[C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25][N:24]2[C:33](OC2C=CC([N+]([O-])=O)=CC=2)=[O:34])=[CH:19][CH:18]=1.O>C1COCC1>[CH3:9][N:8]([CH3:10])[C:6]([C:5]1[CH:11]=[CH:12][C:2]([NH:1][C:33]([N:24]2[CH2:25][CH2:26][C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:23]2[C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:45])([F:15])[F:46])=[CH:18][CH:19]=2)=[O:34])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2355274-Amino-N,N-dimethylbenzamideHCID 59536297(R)-4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 59536420HCID 59536420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-N,N-dimethylbenzamide (74 mg, 452 μmol) in THF (0.5 mL) was added sodium hydride, 60% dispersion in mineral oil (19 μL, 452 μmol). The resulting mixture was then subjected to a microwave irradiation at 150° C. for 5 min. Then, (R)-4-nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 226 μmol, example 88) was added and the mixture was stirred at RT for overnight. Then, H2O (0.5 mL) was added slowly and the mixture was extracted with EtOAc (2×1 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was dissolved in DMSO (1.0 mL) and the solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired compound, which was dissolved in MeOH (1.0 mL). Then, the solution was washed through PL-HCO3 MP-Resin (200 mg per 6 mL tube) and the resin was washed with MeOH (2×0.3 mL). The combined washings were concentrated and dried under vacuum to give the title compound as light brown solid. MS (ESI, positive ion) m/z: 468 (M+H).

Workup

  1. customThe resulting mixture was then subjected to a microwave irradiation at 150° C. for 5 min
  2. extractionthe mixture was extracted with EtOAc (2×1 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in DMSO (1.0 mL)
  6. customthe solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-db210f1ab71c413b895c6746c8b271b5
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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