Ethyl chloroformate → HCID 58968700, compound

HRID 2075095Notes

Reaction equation

HRID 2075095 reaction equation
[CH3:1][O:2][C:3]1([C:9]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:10]=2[CH2:11][N:12]([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:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.Cl[C:52]([O:54][CH2:55][CH3:56])=[O:53]>C(Cl)Cl>[F:29][C:26]([F:28])([F:27])[C:24]1[CH:25]=[C:20]([CH:21]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:23]=1)[CH2:19][N:12]([CH2:11][C:10]1[CH:34]=[C:35]([C:38]([F:41])([F:39])[F:40])[CH:36]=[CH:37][C:9]=1[C:3]1([O:2][CH3:1])[CH2:4][CH2:5][N:6]([C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH2:7][CH2:8]1)[C:13]1[N:14]=[N:15][N:16]([CH3:18])[N:17]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 58968628HCID 58968628, compound

Product 1

HCID 58968700HCID 58968700, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(2-(4-methoxypiperidin-4-yl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (31 mg; 0.049 mmol) in methylene chloride (0.5 mL) was added diisopropylethylamine (0.05 mL; 0.287 mmol). Ethyl chloroformate (10uL; 0.104 mmol) was then added. The resulting reaction was stirred at room temperature for 16 hours. The reaction was filtered over a column of silica/sodium sulfate and concentrated under reduced pressure. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (30-85% ethyl acetate in heptane) to give 32 mg (98%) of a gum. MS (ES+): Calc: 668.5, Found: 669.6 (M+H), 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (s, 1H), 7.73 (s, 2H), 7.51 (d, J=6.64 Hz, 1H), 7.50 (s, 1H), 7.36 (d, J=8.71 Hz, 1H), 5.10 (s, 2H), 4.82 (s, 2H), 4.2 (s, 3H), 4.14 (q, J=7.05, 2H), 4.02 (bm, 2H), 3.16 (t, J=12.45 Hz, 2H), 2.95 (s, 3H), 2.14 (m, 2H), 1.9-1.63 (m, 2H), 1.27 (t, J=7.05 Hz, 3H).

Workup

  1. customThe resulting reaction
  2. filtrationThe reaction was filtered over a column of silica/sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (30-85% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-08f131f90841467182b22495c31e1e77
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

Loading…