Ammonia → HCID 58941397, compound

HRID 747629Notes

Reaction equation

HRID 747629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12])[CH:6]([C:24](O)=[O:25])[CH:5]2[C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[F:34].C(N1CC[O:40][CH2:39][CH2:38]1)C.ClC(OCC)=O.[NH3:49]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:7]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)(=[O:12])=[O:13])[CH:6]([O:40][CH2:39][CH3:38])[C:24]([NH2:49])=[O:25])=[C:4]([CH2:5][C:27]2[C:28]([F:34])=[CH:29][CH:30]=[CH:31][C:32]=2[F:33])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 10928Ethyl chloroformateHCID 69221454HCID 69221454, compound

Product 1

HCID 58941397HCID 58941397, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.34 g of 5-chloro-3-(2,6-difluorophenyl)-1-[(3,4-dimethoxyphenyl)sulfonyl]indoline-2-carboxylic acid in 10 ml of tetrahydrofuran are successively added, at 0° C., 90 μl of N-ethylmorpholine and 68 μl of ethyl chloroformate, the mixture is left at this temperature for 30 minutes, and 0.5 ml of 6M aqueous ammonia solution is introduced. The reaction medium is concentrated and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a dichloromethane/methanol mixture (100% dichloromethane to 98% dichloromethane/2% methanol) to give 0.256 g of product (99.6% HPLC purity).

Workup

  1. concentrationThe reaction medium is concentrated
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a dichloromethane/methanol mixture (100% dichloromethane to 98% dichloromethane/2% methanol)

Sources & evidence

ORD record
ord-12f8cde0acd74d4ca70ff36e5419715c
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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