Water → HCID 71280109, compound

HRID 246609Notes

Reaction equation

HRID 246609 reaction equation
[F: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][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[Si:35]([O:42][CH2:43][CH2:44][C:45]([CH3:48])([NH2:47])[CH3:46])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].O>CN(C=O)C.CN(C1C=CN=CC=1)C>[Si:35]([O:42][CH2:43][CH2:44][C:45]([NH:47][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]([F:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[N:13]=2)[NH:18][CH:19]=1)=[O:23])([CH3:48])[CH3:46])([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 86678000HCID 86678000, compound

Product 1

HCID 71280109HCID 71280109, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.32 mmol) in 6 mL of DMF were added EDCI (123 mg, 0.64 mmol), 4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-amine (139 mg, 0.64 mmol) and DMAP (78 mg, 0.64 mmol) in one portion at room temperature and stirred for 16 hours. The reaction mixture was poured into 35 mL of water filtered and the solid obtained was passed through a pad of silica gel (200-300 mesh, eluting with a mixture of methanol and ethyl acetate (1:20, v/v) to give N-(4-(tert-butyldimethylsilyloxy)-2-methylbutan-2-yl)-2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (70 mg, 42.8%) as a pale yellow solid which was used for the next step without further purification. MS: (M+H)+=511.2.

Workup

  1. filtrationfiltered
  2. customthe solid obtained
  3. washeluting with a mixture of methanol and ethyl acetate (1:20

Sources & evidence

ORD record
ord-5649c9f97c614592b3bb352f15f10a2e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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