Ammonia → HCID 58968747, compound

HRID 2075050Notes

Reaction equation

HRID 2075050 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.CCN(C(C)C)C(C)C.[C:52](Cl)(Cl)=[O:53].C1(C)C=CC=CC=1.N.[CH2:64]([OH:66])[CH3:65]>C(Cl)Cl>[CH2:64]([O:66][C:52]([N:40]1[CH2:39][CH2:38][CH:37]([CH:3]([C:4]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:5]=2[CH2:6][N:7]([CH2:14][C:15]2[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]=2)[C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)[O:2][CH3:1])[CH2:42][CH2:41]1)=[O:53])[CH3:65]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 702EthanolHCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 58968730HCID 58968730, compound

Product 1

HCID 58968747HCID 58968747, compoundYield 34%

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 (19.4 mg, 0.032 mmol) in methylene chloride (0.5 mL) at room temperature was added Hunig's base (8.9 mg, 12 μL, 0.069 mmol) followed by phosgene in toluene (20%, 25 μL, 0.048 mmol). The mixture was stirred at room temperature for 3 hours. Ammonia in ethanol (1 mL) was added and 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 0-50% ethyl acetate in hexane) to afford the title compound (7.4 mg, 34%). 1H NMR (400 MHz, CDCl3) δ ppm 1.11-1.18(m, 1H) 1.20-1.31 (m, 2H) 1.24(t, J=7.05 Hz, 3H) 1.61-1.71 (m, 1H) 1.85(d, J=12.86 Hz, 1H) 2.56 (q, J=14.94 Hz, 2H) 3.04 (s, 3H) 4.05-4.19 (m, 2H) 4.10 (q, J=7.05 Hz, 2H) 4.16 (d, J=7.05 Hz, 1H) 4.21 (s, 3H) 4.68 (d, J=15.77 Hz, 1H) 4.71 (s, 2H) 4.88 (d, J=15.77 Hz, 1H) 7.36 (s, 1H) 7.50 (d, J=7.88 Hz, 1H) 7.58 (d, J=8.71 Hz, 1H) 7.64 (s, 2H) 7.78 (s, 1H). MS (ES+) Calc: 682.6, Found: 683.6 (M+1)

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customSolvent was removed in vacuo The residue
  3. customwas purified by chromatography over 12+S Biotage silica column (eluted with 0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c864bacb11ae4dca894ffea7aaff5adb
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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