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

HRID 415754Notes

Reaction equation

HRID 415754 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-d74e39c1674f4689986937f8f3dcf00c
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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