Dimethylformamide → HCID 58968627, compound

HRID 2075111Notes

Reaction equation

HRID 2075111 reaction equation
[CH3:1][O:2][C:3]1([C:10]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:11]=2[CH2:12][N:13]([CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C:14]2[N:15]=[N:16][N:17]([CH3:19])[N:18]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O.BrC[CH2:56][O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]>CC1CCCO1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1([C:10]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][C:11]=2[CH2:12][N:13]([CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C:14]2[N:15]=[N:16][N:17]([CH2:19][CH2:56][O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[N:18]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 24853310HCID 24853310, compound

Product 1

HCID 58968627HCID 58968627, compoundYield 70%

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)-2-methyl-2H-tetrazol-5-amine (51 mg; 0.086 mmol) in 2-methyltetrahydrofuran (1.0 mL) was added sodium carbonate (38 mg; 0.358 mmol), N,N-dimethylformamide (0.4 mL) and (2-bromoethoxy)-tert-butyldimethylsilane (100 mg; 0.418 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 over sodium sulfate and concentrated in vacuo. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-35% ethyl acetate in heptane) to give 45 mg (70% yield) of a colorless gum. 1H NMR (400 MHz CDCl3) δ ppm 7.77 (s, 1H), 7.73 (s, 2H), 7.47 (d, J=9.96 Hz, 2H), 7.41 (d, J=8.30 Hz, 1H), 5.11 (s, 2H), 4.80 (s, 2H), 4.55 (t, J=5.39 Hz 2H), 4.08 (t, J=5.39 Hz, 2H), 2.94 (s, 3H), 2.12 (m, 2H), 1.98 (m, 2H), 1.8-1.45 (m, 8H), 0.82 (s, 9H), −0.07 (s, 6H).

Workup

  1. customReaction
  2. washwashed twice with water
  3. dry with materialThe organic was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-35% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-67d178e5cb0e4ceb920a6db92bc02887
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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