HCID 86640143, compound → HCID 15985054, compound

HRID 2408438Notes

Reaction equation

HRID 2408438 reaction equation
O1CCCCC1[O:7][NH:8][C:9](=[O:43])/[CH:10]=[CH:11]/[C:12]1[CH:16]=[CH:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][S:33]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)(=[O:35])=[O:34])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:13]=1>CO>[OH:7][NH:8][C:9](=[O:43])/[CH:10]=[CH:11]/[C:12]1[CH:16]=[CH:15][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][S:33]([C:36]4[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=4)(=[O:35])=[O:34])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH:13]=1

Participants

3

Reactant 1

HCID 86640143HCID 86640143, compound

Product 1

HCID 15985054HCID 15985054, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.278 g (E)-N-(tetrahydro-pyran-2-yloxy)-3-{1-[4′-(toluene-4-sulfonylamino)-biphenyl-4-sulfonyl]-1H-pyrrol-3-yl}-acrylamide with 6.0 ml methanol and 13.0 ml 1M aqueous HCL is stirred at ambient temperature for 2 days. In case of incomplete deprotection the suspension is treated again with 1M aqueous HCL until the reaction is at completion. The mixture is evaporated and the resulting solid is washed with water and diisopropylether. The crude product is isolated by PLC plates chromatography. By this method 0.129 g of a red solid are obtained. Melting point: 119-126° C., sinter is beginning from 97° C.

Workup

  1. additionIn case of incomplete deprotection the suspension is treated again with 1M aqueous HCL until the reaction
  2. customThe mixture is evaporated
  3. washthe resulting solid is washed with water and diisopropylether
  4. customThe crude product is isolated by PLC plates chromatography

Sources & evidence

ORD record
ord-9e91351651774360a92d10ea31f61000
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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