Azetidine → HCID 58116818, compound

HRID 38574Notes

Reaction equation

HRID 38574 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:28][CH2:27][C:10]2[C:11]3[C:16]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:26][C:9]=2[CH2:8]1)=[O:6].[NH:29]1[CH2:32][CH2:31][CH2:30]1>CN(C=O)C.C(OC)(C)(C)C>[N:29]1([CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]2[CH2:28][CH2:27][C:10]3[C:11]4[C:16]([NH:17][C:18]5[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=5)=[N:15][CH:14]=[N:13][C:12]=4[S:26][C:9]=3[CH2:8]2)=[O:6])[CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 10422AzetidineHCID 581168067-[(2E)-4-Chlorobut-2-enoyl]-N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 58116818HCID 58116818, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of Example 59A (100 mg, 0.20 mmol) in DMF (2 mL) was added azetidine (23 mg, 0.40 mmol), and the mixture was heated to 50° C. for 1 h. It was then diluted with methyl tert-butyl ether, washed with water and dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by preparative HPLC to yield 12.4 mg (13%) of the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b14fb602a6084f86af920b435502f39d
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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