Thiomorpholine → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-[3,5-dimethyl-4-(thiomorpholine-4-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359782Notes

Reaction equation

HRID 1359782 reaction equation
N1C2C(=NC=CC=2)N([O:10][C:11]([C:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[C:20]3\[C:21](=[O:41])[NH:22][C:23]4[C:28]\3=[CH:27][C:26]([S:29]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])(=[O:31])=[O:30])=[CH:25][CH:24]=4)[NH:15][C:14]=2[CH3:42])=O)N=1.[NH:43]1[CH2:48][CH2:47][S:46][CH2:45][CH2:44]1>CC(N(C)C)=O>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[CH2:32][S:29]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:41])/[C:20]/2=[CH:19]\[C:16]1[NH:15][C:14]([CH3:42])=[C:13]([C:11]([N:43]2[CH2:48][CH2:47][S:46][CH2:45][CH2:44]2)=[O:10])[C:17]=1[CH3:18])(=[O:30])=[O:31]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 137178925HCID 137178925, compound

Product 1

HCID 590776885-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-[3,5-dimethyl-4-(thiomorpholine-4-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester (100 mg, 0.162 mmol) in DMA (2 mL) was added thiomorpholine (33 mg, 2 eq.). The mixture was stirred at rt for 2 hours. The reaction was concentrated, diluted with DCM, washed with sat. NaHCO3 and water, concentrated and triturated with methanol to give the titled compound as an orange solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3 and water
  4. concentrationconcentrated
  5. customtriturated with methanol

Sources & evidence

ORD record
ord-db705bfd1c074659bcc8b294f3214d47
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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