Hydrochloric Acid → HCID 68299301, compound

HRID 532497Notes

Reaction equation

HRID 532497 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]4)[C:14]=3[S:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:37].Cl>CN(C)C=O>[CH3:37][N:20]([C:19]1[C:14]2[S:13][CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=3)[C:15]=2[N:16]=[CH:17][N:18]=1)[CH:21]1[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57414212HCID 57414212, compound

Product 1

HCID 68299301HCID 68299301, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

54 mg (0.11 mmol) of tert-butyl 4-(7-(4-methanesulfonyl-phenyl)thieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate obtained in Example 109 was dissolved in 2 ml of N,N-dimethylformamide, and 3.4 mg (0.143 mmol) of NaH was added thereto. After 0.5 hr, 10 μl (0.143 mmol) of iodomethane was dropwise added to the mixture at room temperature, heated to 50° C. and stirred for 3 hr. The resulting mixture was neutralized with 1 N aqueous hydrochloride, and extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure to obtain 40 mg of the title compound as a pale yellow solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-894fb4dfbcd54a39b1653caaec3c7a9d
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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