Ammonia → HCID 58968727, compound

HRID 2075048Notes

Reaction equation

HRID 2075048 reaction equation
[CH3:1][O:2][CH:3]([CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[C:4]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:5]=1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.CC[N:45]([CH:49](C)C)C(C)C.C(Cl)(Cl)=[O:53].C1(C)C=CC=CC=1.N>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=1)[CH2:14][N:7]([CH2:6][C:5]1[CH:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:4]=1[CH:3]([O:2][CH3:1])[CH:37]1[CH2:38][CH2:39][N:40]([C:49]([NH2:45])=[O:53])[CH2:41][CH2:42]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 58968730HCID 58968730, compound

Product 1

HCID 58968727HCID 58968727, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-(methoxy(piperidin-4-yl)methyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (19.5 mg, 0.030 mmol) in methylene chloride (0.2 mL) at room temperature was added Hunig's base (7 mg, 10 μL, 0.06 mmol) followed by phosgene in toluene (20%, 25 μL, 0.048 mmol). The mixture was stirred at room temperature for 1 hour. Aqueous ammonia (0.2 mL) was added. The mixture was stirred at room temperature overnight. Solvent was removed in vacuo. The residue was purified by chromatography over 12+S Biotage silica column (eluted with 1-7% methanol in methylene chloride) to afford the title compound (13 mg, 62%). 1H NMR (400 MHz, CDCl3) δ ppm 1.15-1.21 (m, 1H) 1.23-1.37(m, 2H) 1.61-1.76(m, 3H) 1.88(d, J=12.45 Hz, 1H) 2.57-2.73 (m, 2H) 3.04 (s, 3H) 3.86-3.97 (m, 2H) 4.18 (d, J=7.05 Hz, 1H) 4.21 (s, 3H) 4.66-4.73 (m, 3H) 4.87 (d, J=16.18 Hz, 1H) 7.36 (s, 1H) 7.50 (d, J=7.88 Hz, 1H) 7.58 (d, J=8.30 Hz, 1H) 7.64 (s, 2H) 7.78 (s, 1H). MS (ES+) Calc: 653.2, Found: 654.6 (M+1)

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customSolvent was removed in vacuo
  3. customThe residue was purified by chromatography over 12+S Biotage silica column (eluted with 1-7% methanol in methylene chloride)

Sources & evidence

ORD record
ord-1f46261223274f77a12b70b676ceeed8
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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