Water → HCID 86698052, compound

HRID 518900Notes

Reaction equation

HRID 518900 reaction equation
C([N:3]1[C:7]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[N:20]=[CH:21][C:22]5[S:27][C:26]([C:28](N)=[O:29])=[C:25]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=6[O:37][CH3:38])[C:23]=5[N:24]=4)=[C:14]([O:39][CH:40]([CH3:42])[CH3:41])[CH:13]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4]1)=O.[OH-:43].[Na+].O>CO>[NH:3]1[C:7]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[N:20]=[CH:21][C:22]5[S:27][C:26]([C:28]([OH:43])=[O:29])=[C:25]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=6[O:37][CH3:38])[C:23]=5[N:24]=4)=[C:14]([O:39][CH:40]([CH3:42])[CH3:41])[CH:13]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86698053HCID 86698053, compound

Product 1

HCID 86698052HCID 86698052, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 76 mg of 2-{[4-(1-formyl-1,7-diazaspiro[4.4]non-7-yl)-2-(propan-2-yloxy)phenyl]amino}-7-(2-methoxyphenyl)thieno[3,2-d]pyrimidine-6-carboxamide and 2 ml of 5N sodium hydroxide in 15 ml of methanol is stirred at ambient temperature for 3 hours, and then maintained at reflux for 1 h 30. The mixture is stirred at AT for 15 h and then again maintained at reflux for 5 h 30. The reaction medium is then run into 20 ml of water and then the methanol is eliminated by concentration under reduced pressure. The resulting aqueous phase is washed several times with dichloromethane (3 times 20 ml) and then acidified so as to obtain a pH with a value of about 7/8, and then the aqueous phase is extracted a further three times with 20 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain 72 mg of 2-{[4-(1,7-diazaspiro[4.4]non-7-yl)-2-(propan-2-yloxy)phenyl]amino}-7-(2-methoxyphenyl)thieno[3,2-d]pyrimidine-6-carboxylic acid in the form of a brown solid.

Workup

  1. temperaturemaintained
  2. temperatureat reflux for 1 h 30
  3. stirringThe mixture is stirred at AT for 15 h
  4. temperatureagain maintained
  5. temperatureat reflux for 5 h 30
  6. concentrationthe methanol is eliminated by concentration under reduced pressure
  7. washThe resulting aqueous phase is washed several times with dichloromethane (3 times 20 ml)
  8. customto obtain a pH with a value of about 7/8
  9. extractionthe aqueous phase is extracted a further three times with 20 ml of dichloromethane
  10. dry with materialThe combined organic phases are dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-11222549141a406282d9d632c0281262
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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