Cesium carbonate → tert-Butyl 3-(3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-5-(difluoromethoxy)-1H-indazol-1-yl)propyl(methyl)carbamate

HRID 246517Notes

Reaction equation

HRID 246517 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[NH:19][N:18]=3)[N:15]=2)[N:10]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:39][CH2:40][CH2:41][N:42]([CH3:50])[C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:28])[F:29])[CH:24]=4)[N:19]([CH2:39][CH2:40][CH2:41][N:42]([CH3:50])[C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[N:18]=3)[N:15]=2)[N:10]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14194551tert-Butyl (3-chloropropyl)methylcarbamateHCID 712795662-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Product 1

HCID 71280007tert-Butyl 3-(3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-5-(difluoromethoxy)-1H-indazol-1-yl)propyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-tert-Butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (280 mg, 528 μmol), tert-butyl 3-chloropropyl(methyl)carbamate (110 mg, 528 μmol) and cesium carbonate (516 mg, 1.58 mmol) in dimethylformamide (4 mL) were heated in a microwave at 100° C. for 30 min. The mixture was partitioned between ethyl acetate and water, then the organic phase washed with water 3 times, dried, filtered and concentrated. The crude residue was used in the next step without purification. MS (M+H)+=702.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic phase washed with water 3 times
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-0d6f734ad65f4d508bf9d48ae4fcab01
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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