Water → HCID 10338960, compound

HRID 227491Notes

Reaction equation

HRID 227491 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=[O:12])=[C:5]2[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:30][CH2:31][CH3:32].O>CN(C)C=O>[N:17]1([S:14]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([O:1][CH2:30][CH2:31][CH3:32])[CH:3]=3)[NH:7][C:6]=2[C:11]([NH2:13])=[O:12])(=[O:16])=[O:15])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 336431-Iodopropane2×HCID 10314224HCID 10314224, compound

Product 1

HCID 10338960HCID 10338960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide from Example 50 (29 mg, 0.089 mmol) in 1 mL of dimethylformamide was added cesium carbonate (86 mg, 0.27 mmol) and 1-iodopropane (0.0094 mL, 0.096 mmol). After one hour, another portion (0.005 mL) of 1-iodopropane was added. After an additional hour, 0.5 mL of water was added to solubilize the material, and the resulting mixture was purified by preparative reversed phase HPLC to provide the titled product as a white solid. HRMS (ES) exact mass calculated for C16H22N3O5S (M+H+): 368.1275. Found 368.1291.

Workup

  1. waitAfter an additional hour
  2. customthe resulting mixture was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-c32765b5058941219f55487edde82427
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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