1-Chloro-N,N-2-trimethylpropenylamine → HCID 118435542, compound

HRID 629818Notes

Reaction equation

HRID 629818 reaction equation
ClC(N(C)C)=C(C)C.[Br:9][C:10]1[N:11]=[C:12]([C@@:15]2([NH:24][C:25]([NH:27][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[S:26])[C@H:20]([CH2:21]O)[CH2:19][C@H:18]([CH3:23])[O:17][CH2:16]2)[S:13][CH:14]=1>ClCCl>[Br:9][C:10]1[N:11]=[C:12]([C@:15]23[CH2:16][O:17][C@@H:18]([CH3:23])[CH2:19][C@H:20]2[CH2:21][S:26][C:25]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:24]3)[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 118435603HCID 118435603, compound

Product 1

HCID 118435542HCID 118435542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (Ghosez's reagent, 7.85 mL, 59.3 mmol) was added drop-wise to a solution of C5 (9.30 g, 19.8 mmol) in dichloromethane (200 mL). After 1 hour at room temperature, the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) provided the product as a solid. Yield: 6.90 g, 15.2 mmol, 77%. LCMS m/z 452.1, 454.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 13.69 (br s, 1H), 8.38-8.43 (m, 2H), 7.64-7.70 (m, 1H), 7.54-7.60 (m, 2H), 7.34 (s, 1H), 4.45 (d, J=12.5 Hz, 1H), 3.93 (d, J=12.5 Hz, 1H), 3.74-3.83 (m, 1H), 3.28-3.36 (m, 1H), 3.23 (dd, J=13.5, 4.0 Hz, 1H), 2.77 (dd, J=13.5, 2.8 Hz, 1H), 1.66-1.82 (m, 2H), 1.32 (d, J=6.2 Hz, 3H).

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f0ecba10e4e43639fc9fc114c851c32
Source dataset
uspto-grants-2016_04
Patent number
US09315520B2

Reaction notes

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