Dimethylformamide dimethyl acetal → HCID 50991561, compound

HRID 220412Notes

Reaction equation

HRID 220412 reaction equation
[CH:1]1([N:4]([CH:26]2[CH2:28][CH2:27]2)[C:5]([C:7]2[N:23]([CH2:24][CH3:25])[C:10]3=[N:11][C:12]([NH:19][C:20]([NH2:22])=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.CO[CH:31](OC)[N:32](C)C.C1(C)C=C(C)C=C(C)C=1S(ON)(=O)=O>O>[S:21]1[C:20]([NH:19][C:12]2[N:11]=[C:10]3[N:23]([CH2:24][CH3:25])[C:7]([C:5]([N:4]([CH:1]4[CH2:2][CH2:3]4)[CH:26]4[CH2:27][CH2:28]4)=[O:6])=[CH:8][C:9]3=[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=23)=[N:22][CH:31]=[N:32]1

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 58180527N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Product 1

HCID 50991561HCID 50991561, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 2B, 30 mg, 0.075 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (1 g, 8.39 mmol) was heated at 50° C. for 2 h. Excess 1,1-dimethoxy-N,N-dimethylmethanamine was evaporated in vacuo and the crude example was dissolved in dichloromethane (1 mL) and O-(mesitylsulfonyl)hydroxylamine (24.4 mg, 0.113 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. Water was added and the layers were separated. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by preparative HPLC to give 4-(1,2,4-thiadiazol-5-ylamino)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (7 mg, 19.20% yield) as a yellow solid.

Workup

  1. customExcess 1,1-dimethoxy-N,N-dimethylmethanamine was evaporated in vacuo
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5eeb704419cc4d0ebdbbff9d1294a11d
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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