Thioacetamide → HCID 50991652, compound

HRID 220408Notes

Reaction equation

HRID 220408 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[N:11]=[C:10]2[N:12]([CH2:24][CH3:25])[C:13]([C:15]([N:17]([CH:21]3[CH2:23][CH2:22]3)[CH:18]3[CH2:20][CH2:19]3)=[O:16])=[CH:14][C:9]2=[C:8]2[N:26]([CH3:29])[CH:27]=[N:28][C:7]=12)=O.[C:30]([NH2:33])(=[S:32])[CH3:31]>CN(C=O)C>[CH:18]1([N:17]([CH:21]2[CH2:23][CH2:22]2)[C:15]([C:13]2[N:12]([CH2:24][CH3:25])[C:10]3=[N:11][C:6]([NH:5][C:3]4[N:33]=[C:30]([CH3:31])[S:32][CH:2]=4)=[C:7]4[N:28]=[CH:27][N:26]([CH3:29])[C:8]4=[C:9]3[CH:14]=2)=[O:16])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 58180534HCID 58180534, compound

Product 1

HCID 50991652HCID 50991652, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-chloroacetamido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (58.5 mg, 0.141 mmol) in DMF (176 μL) was added thioacetamide (12.71 mg, 0.169 mmol). The vial was capped and the reaction mixture was heated at 80° C. 3 h. The reaction mixture was concentrated in vacuo. The crude residue was taken up in MeOH and purified by prep-HPLC. N,N-Dicyclopropyl-6-ethyl-1-methyl-4-(2-methylthiazol-4-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (4.05 mg, 6.6% yield) was isolated as an off-white solid.

Workup

  1. customThe vial was capped
  2. custom3 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-edfa80bd28384ba59b483f65abf8ccd4
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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