Dimethylformamide → HCID 90014780, compound

HRID 930966Notes

Reaction equation

HRID 930966 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1.CN(C)C=O.[CH3:32][CH:33]([CH3:37])[C:34](Cl)=[O:35].C(N(CC)CC)C>O>[CH3:32][CH:33]([CH3:37])[C:34]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1)=[O:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 90014477HCID 90014477, compound

Product 1

HCID 90014780HCID 90014780, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 50 mg (130 μmol) (RS)-6-{[7-(aminomethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 20), 5 mL N,N-dimethylformamide, 13.7 μL 2-methylpropanoyl chloride and 18.2 mL N,N-diethylethanamine was stirred at 23° C. overnight. Water was added and the solvents were removed. The residue was purified by chromatography to give 16 mg (26%) of the title compound.

Workup

  1. customthe solvents were removed
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6177fad974b544fb8fbe877055e65e85
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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