Dimethylcarbamoyl Chloride → HCID 74928829, compound

HRID 504497Notes

Reaction equation

HRID 504497 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[CH:12]1[CH2:17][C:16](=[O:18])[NH:15][CH:14]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[CH3:26])[C:13]21[C:34]1[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=1)[NH:28][C:27]2=[O:36].[CH3:37][N:38]([CH3:42])[C:39](Cl)=[O:40].C(N(CC)CC)C>>[Cl:35][C:31]1[CH:30]=[C:29]2[NH:28][C:27](=[O:36])[C:13]3([CH:12]([C:6]4[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=4[O:4][CH2:3][CH2:2][NH:1][C:39]([N:38]([CH3:42])[CH3:37])=[O:40])[CH2:17][C:16](=[O:18])[NH:15][CH:14]3[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[CH3:26])[C:34]2=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 68962225HCID 68962225, compound

Product 1

HCID 74928829HCID 74928829, compoundYield 21.9%

Procedure

At room temperature, a mixture of racemic (2′S,3S,4′R)-4′-[2-(2-amino-ethoxy)5-chloro-phenyl]-6-chloro-2′-(5-fluoro-2-methyl phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.076 mmol), dimethylcarbamoyl chloride (41 mg, 0.379 mmol) and triethylamine (38 mg, 0.379 mmol) was stirred 0.5 h. Then the mixture was filtered, concentrated and the residue was purified by Prep-HPLC to give the title compound as a white solid (10 mg).

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-5e4a220c529347f08eb1f119249be4c5
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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