1,2-Dichloroethane → HCID 71279835, compound

HRID 246440Notes

Reaction equation

HRID 246440 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([OH:23])=O)=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:46][C:47]([NH2:50])([CH3:49])[CH3:48]>CN(C=O)C.C(OCC)(=O)C>[C:47]([NH:50][C:21]([C:20]1[C:14]2[C:15](=[N:16][CH:17]=[C:12]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[N:13]=2)[N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])[CH:19]=1)=[O:23])([CH3:49])([CH3:48])[CH3:46]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6385Tert-ButylamineHCID 757711-HydroxybenzotriazoleHCID 712796712-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 71279835HCID 71279835, compoundYield 112.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (111 mg, 242 μmol) in DMF (4 mL) was added EDC (107 mg, 557 μmol), HOBT (107 mg, 557 μmol) and 2-methylpropan-2-amine (78.6 mg, 0.113 mL, 1.08 mmol) at 20° C. After 3 h the reaction mixture was diluted with ethyl acetate and washed with 10% citric acid solution. The organic layer was then washed with saturated sodium bicarbonate and brine then dried (sodium sulfate), filtered and concentrated in vacuo to give the crude N-tert-butyl-2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg) as a light brown oil. This was used directly in the next step without further purification.

Workup

  1. washwashed with 10% citric acid solution
  2. washThe organic layer was then washed with saturated sodium bicarbonate and brine
  3. dry with materialthen dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfa44d37c7054041955dc05c22e60098
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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