Dimethylformamide → HCID 118119944, compound

HRID 930969Notes

Reaction equation

HRID 930969 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.[C:32](Cl)(=[O:37])[O:33][CH:34]([CH3:36])[CH3:35].C(N(CC)CC)C>O>[O:23]=[C:21]1[NH:20][C:19]2[CH:24]=[CH:25][C:16]([NH:15][C:14]3[C:9]4[C:6]5[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:32](=[O:37])[O:33][CH:34]([CH3:36])[CH3:35])[CH2:4][C:5]=5[S:26][C:10]=4[N:11]=[CH:12][N:13]=3)=[CH:17][C:18]=2[S:22]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 90014477HCID 90014477, compound

Product 1

HCID 118119944HCID 118119944, compoundYield 40%

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-dimethylforamide, 130 μL isopropyl carbonochloridate (1M in toluene) and 18.2 μL N,N-diethylethanamine was stirred at 23° C. overnight. Water was added, the solvents were removed and the residue purified by chromatography to give 25 mg (40%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-b048f3bb749c48d3971f5407db6b7df3
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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