Trimethylsilyl iodide → N-[2-(4-Aminomethyl-6-chloro-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

HRID 70967Notes

Reaction equation

HRID 70967 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:17]2[C:13](=[N:14][N:15]([CH2:18][C:19]([C:35]#[N:36])([CH3:34])[NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[N:16]=2)[CH:12]=[C:11]([Cl:37])[CH:10]=1)(C)(C)C.C[Si](I)(C)C>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[C:17]2[C:13](=[N:14][N:15]([CH2:18][C:19]([NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)([C:35]#[N:36])[CH3:34])[N:16]=2)[CH:12]=[C:11]([Cl:37])[CH:10]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66621023{6-chloro-2-[2-cyano-2-methyl-2-(4-trifluoromethoxy-benzoylamino)-ethyl]-2H-benzotriazol-4-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 66620415N-[2-(4-Aminomethyl-6-chloro-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {6-chloro-2-[2-cyano-2-methyl-2-(4-trifluoromethoxy-benzoylamino)-ethyl]-2H-benzotriazol-4-ylmethyl}-carbamic acid tert-butyl ester (100 mg) in DCM (2 mL) was added trimethylsilyl iodide (0.05 mL). After 20 minutes, the mixture was quenched with methanol and concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with a saturated solution of sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as a white solid (70 mg, 87%). Rf=0.2 (1:1 EA/heptane). MS (ES): M/Z [M+H]=453. 1H NMR: (500 MHz, CHLOROFORM-d): 1.86 (s, 3H), 4.21 (d, J=3.4 Hz, 2H), 5.16 (d, J=13.7 Hz, 1H), 5.43 (d, J=13.8 Hz, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.33 (d, J=0.7 Hz, 1H), 7.60 (s, 1H), 7.75 (d, J=1.5 Hz, 1H) and 7.88 (d, J=8.7 Hz, 2H). 19F NMR (376 MHz, DMSO-d6): −57.1 (s, 3F).

Workup

  1. customthe mixture was quenched with methanol
  2. concentrationconcentrated under reduced pressure
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15e15a9b9c83483fa29a5174fd545d87
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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