Trimethylsilyl isocyanate → HCID 68696154, compound

HRID 1157675Notes

Reaction equation

HRID 1157675 reaction equation
[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH2:15][C:16]([NH:18][NH2:19])=[O:17])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C[Si]([N:25]=[C:26]=[O:27])(C)C>ClCCl.C(N(C(C)C)CC)(C)C>[C:26]([NH:19][NH:18][C:16](=[O:17])[CH2:15][CH:11]1[CH2:12][CH2:13][CH2:14][N:10]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=1[CH3:20])(=[O:27])[NH2:25]

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 68695159HCID 68695159, compound

Product 1

HCID 68696154HCID 68696154, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2-[1-(3-chloro-4-cyano-2-methylphenyl)pyrrolidin-2-yl]acetohydrazide (0.288 g, 1.030 mmol) in dichloromethane and diisopropylethylamine, add trimethylsilyl isocyanate (0.238 g, 2.060 mmol) and stir the reaction at 21° C. for 2 h. Partition the reaction is between ethyl acetate and brine. Dry the organic phase over magnesium sulphate, filter, and remove the solvent is under reduced pressure to yield the title compound. (0.303 g, 91%) mass spectrum (m/e): 322.1 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.37 (s, 1H) 7.38 (d, 1H), 7.30 (s, 1H), 6.34 (d, 1H), 5.04 (s, 2H), 4.34 (t, 1H), 3.86 (m, 1H), 3.08 (m, 1H), 2.46 (m, 1H), 2.42 (s, 3H), 2.03 (s, 3H), 2.20-1.85 (m. 3H).

Workup

  1. customthe reaction at 21° C. for 2 h
  2. customPartition the reaction
  3. dry with materialDry the organic phase over magnesium sulphate
  4. filtrationfilter
  5. customremove the solvent

Sources & evidence

ORD record
ord-603b4eb96d48441db417e304aa189ec1
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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