HCID 58968656, compound → HCID 58968647, compound

HRID 2075087Notes

Reaction equation

HRID 2075087 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:27]1[CH2:30][CH2:29][CH2:28]1)=[O:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH3:40][Mg]Br>O1CCCC1>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:33]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:27]1[CH2:28][CH2:29][CH2:30]1)([OH:26])[CH3:40])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

4

Reactant 2

HCID 58968656HCID 58968656, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58968647HCID 58968647, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl)(cyclobutyl)methanone (Preparation 29, 28 mg; 0.050 mmol) in tetrahydrofuran (0.5 mL) was added methylmagnesium bromide (50 uL; 0.15 mmol; 3.0M in diethyl ether). The reaction was stirred at room temperature for 2 hours. The reaction was quenched with 2 drops water and 1 drop aqueous 2N hydrochloric acid. The mixture was diluted with ethyl acetate and filtered over a column containing silica gel and sodium sulfate. The crude was purified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-50% ethyl acetate in heptane) to give 22 mg (76% yield) of the title compound as a colorless gum. MS (ES−): Calc: 581.4, Found: 580.6 (M−H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.74 (s, 2H), 7.42 (d, 1H), 7.41 (s, 1H), 7.33 (d, J=9.13 Hz, 1H), 5.27(d, J=16.60 Hz, 1H), 5.15 (d, J=16.18 Hz, 1H), 4.85 (s, 2H), 4.18 (s, 3H), 2.97 (m, 1H), 2.12-1.69 (m, 6H), 1.43 (s, 3H).

Workup

  1. customThe reaction was quenched with 2 drops water and 1 drop aqueous 2N hydrochloric acid
  2. additionThe mixture was diluted with ethyl acetate
  3. filtrationfiltered over a column
  4. additioncontaining silica gel and sodium sulfate
  5. customThe crude was purified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5d0f9c160c6b4998b6f05847e9823f73
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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