Dimethylformamide → HCID 24853310, compound

HRID 2075079Notes

Reaction equation

HRID 2075079 reaction equation
[CH3:1][O:2][C:3]1([C:10]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:11]=2[CH2:12][N:13]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[C:14]2[N:15]=[N:16][NH:17][N:18]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:42](=O)([O-])[O-].[Na+].[Na+].CN(C)C=O.S(OC)(OC)(=O)=O>CC1CCCO1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1([C:10]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][C:11]=2[CH2:12][N:13]([CH2:19][C:20]2[CH:21]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:23]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:25]=2)[C:14]2[N:15]=[N:16][N:17]([CH3:42])[N:18]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 58968673HCID 58968673, compound

Product 1

HCID 24853310HCID 24853310, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine (145 mg; 0.243 mmol) in 2-methyltetrahydrofuran (2.5 mL) was added sodium carbonate (110 mg; 1.03 mmol), N,N-dimethylformamide (1.0 mL) and dimethyl sulfate (70 uL; 0.739 mmol). Reaction was stirred for 16 hours at 60° C. The reaction was diluted with ethyl acetate, washed twice with water and then brine. The organic was dried sodium sulfate and concentrated under reduced pressure. The residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane) to give 120 mg (80.9% yield) of a colorless gum which crystallized into a white solid upon sitting. Melting point: 103-104° C. MS (ES+): Calc: 609.5, Found: 610.5 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.77 (s, 1H), 7.72 (s, 2H), 7.47 (d, J=7.47 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=8.30 Hz, 1H), 5.10 (s, 2H), 4.79 (s, 2H), 4.20 (s, 3H), 2.94 (s, 3H), 2.12 (m, 2H), 1.97 (m, 2H), 1.8-1.46 (m, 8H).

Workup

  1. customReaction
  2. washwashed twice with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-aad361566e7948aeb35409e2850d3887
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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