Water → HCID 59536274, compound

HRID 445343Notes

Reaction equation

HRID 445343 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[H-].[Na+].[F:12][C:13]([F:43])([F:42])[C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22][N:21]2[C:30](OC2C=CC([N+]([O-])=O)=CC=2)=[O:31])=[CH:16][CH:15]=1.O>C1COCC1>[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:30]([N:21]2[CH2:22][CH2:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:20]2[C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:42])([F:12])[F:43])=[CH:15][CH:16]=2)=[O:31])=[CH:3][CH:4]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 38713955-Aminopyridine-2-carbonitrileHCID 59536297(R)-4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 59536274HCID 59536274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-pyridinecarbonitrile (81 mg, 678 μmol) in THF (1.0 mL) was added sodium hydride, 60% dispersion in mineral oil (17 mg, 452 μmol). The resulting mixture was then subjected to a microwave irradiation at 160° C. for 15 min. Then, (R)-4-nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (100 mg, 226 example 88) was added and the mixture was stirred at RT for overnight. Then, H2O (0.5 mL) was added 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 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). The solution was then 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 a light yellow solid. MS (ESI, positive ion) m/z: 423 (M+H).

Workup

  1. customThe resulting mixture was then subjected to a microwave irradiation at 160° C. for 15 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 was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-6348f64cd689466c97c4c98401120ec1
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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