Sodium Carbonate → HCID 118671955, compound

HRID 630493Notes

Reaction equation

HRID 630493 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][NH:21]1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:34]=[N:35][C:36]([N:39]2[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([C:48](O)=[O:49])[CH:46]=3)[C:41]([S:51]([CH3:53])=[O:52])=[CH:40]2)=[N:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:34]=[N:35][C:36]([N:39]2[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([C:48]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][C@@H:20]4[CH3:19])=[O:49])[CH:46]=3)[C:41]([S:51]([CH3:53])=[O:52])=[CH:40]2)=[N:37][CH:38]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 111923Propylphosphonic anhydrideHCID 12012220(3S)-3-methylmorpholineHCID 1186660891-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid

Product 1

HCID 118671955HCID 118671955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

T3P (50 wt % solution in ethyl acetate, 179 μl, 0.304 mmol) was added to a solution of (S)-3-methylmorpholine (46 mg, 0.456 mmol) and 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid (60 mg, 0.152 mmol) in dichloromethane (3 mL) at room temperature and the mixture was stirred overnight. 1 M sodium carbonate solution (20 mL) was poured into the reaction mixture and stirring was continued for 1 h. The mixture was extracted with dichloromethane (3×) and the combined organic layers were dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography [dichloromethane with 0-5% ethanol]. White foam. Yield: 68 mg (93% of theory).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography [dichloromethane with 0-5% ethanol]

Sources & evidence

ORD record
ord-c2149ff1348447269ab5c0cb5c53c176
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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