Hydrochloric Acid → HCID 71745956, compound

HRID 518893Notes

Reaction equation

HRID 518893 reaction equation
Cl.[C:2]([C:5]1[S:13][C:12]2[CH:11]=[N:10][C:9]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[CH:17][C:16]=3[O:34][CH:35]([CH3:37])[CH3:36])=[N:8][C:7]=2[C:6]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[O:44][CH3:45])(=[O:4])[NH2:3]>C(OCC)(=O)C>[CH3:45][O:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[C:6]1[C:7]2[N:8]=[C:9]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:17][C:16]=3[O:34][CH:35]([CH3:37])[CH3:36])[N:10]=[CH:11][C:12]=2[S:13][C:5]=1[C:2]([NH2:3])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86698044HCID 86698044, compound

Product 1

HCID 71745956HCID 71745956, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 1M solution of hydrochloric acid in ethyl acetate (90 ml) is added slowly to a mixture of 536 mg of 2-methylpropan-2-yl 4-[4-{[6-carbamoyl-7-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-2-yl]amino}-3-(propan-2-yloxy)phenyl]piperidine-1-carboxylate in 5 ml of cold ethyl acetate in an ice bath. After the addition, the mixture is stirred at ambient temperature for 18 h, and then the precipitate is filtered off and rinsed with ether. The solid is suspended in 60 ml of water and 40 ml of a 1M sodium hydroxide solution are added and the mixture is left to stir for 5 min. The mixture is extracted three times with 100 ml of ethyl acetate. The organic phases are washed with 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is taken up with ether and the solid is filtered off and dried under vacuum, so as to obtain 321 mg of 7-(2-methoxyphenyl)-2-{[4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl]amino}thieno[3,2-d]pyrimidine-6-carboxamide in the form of a yellow solid.

Workup

  1. additionAfter the addition
  2. filtrationthe precipitate is filtered off
  3. washrinsed with ether
  4. addition40 ml of a 1M sodium hydroxide solution are added
  5. waitthe mixture is left
  6. stirringto stir for 5 min
  7. extractionThe mixture is extracted three times with 100 ml of ethyl acetate
  8. washThe organic phases are washed with 50 ml of water
  9. dry with materialThe organic phases are dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. filtrationthe solid is filtered off
  13. customdried under vacuum

Sources & evidence

ORD record
ord-2e3995445edd4aa8ba3d1016c256baf3
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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