Dimethylcarbamoyl Chloride → HCID 18727257, compound

HRID 609693Notes

Reaction equation

HRID 609693 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[S:18]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[C:35]3[C:30](=[C:31]([F:39])[C:32]([F:38])=[C:33]([F:37])[C:34]=3[F:36])[NH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:20])=[O:19])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][N:41]([CH3:45])[C:42](Cl)=[O:43]>C(Cl)Cl>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[CH2:17][N:16]([C:42]([N:41]([CH3:45])[CH3:40])=[O:43])[CH2:15][CH2:14][N:13]1[S:18]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[C:35]3[C:30](=[C:31]([F:39])[C:32]([F:38])=[C:33]([F:37])[C:34]=3[F:36])[NH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:20])=[O:19])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 18727251HCID 18727251, compound

Product 1

HCID 18727257HCID 18727257, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyloxy-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (12 g, 21.08 mmol) [prepared as described in Step 5 above] and 2,6-luitidine (4.0 ml, 33.73 mmol) in methylene chloride (100 ml) was treated with dimethylcarbamoyl chloride (3.10 ml, 33.73 mmol) and stirred for 14 h. The reaction mixture was washed with 3M aqueous HCl solution (20 ml), brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed (SiO2, 30% ethyl acetate/hexane then 5% methanol/methylene chloride). The product was dissolved in ethyl acetate (25 ml) and added dropwise to hexane (200 ml) with vigorous stirring. The solid was filtered to give N-benzyloxy-4-(N,N-dimethylaminocarbonyl)-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1sulfonyl]piperazine-2-(R)-carboxamide (67%) as a white solid.

Workup

  1. washThe reaction mixture was washed with 3M aqueous HCl solution (20 ml), brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed (SiO2, 30% ethyl acetate/hexane
  5. dissolutionThe product was dissolved in ethyl acetate (25 ml)
  6. additionadded dropwise to hexane (200 ml) with vigorous stirring
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-8229929bd97d4a4585fa925ff2a2aa5e
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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