1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71280441, compound

HRID 246685Notes

Reaction equation

HRID 246685 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[N:12]=[C:13]4[C:19]([C:20](O)=[O:21])=[CH:18][NH:17][C:14]4=[N:15][CH:16]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[Si:43]([O:50][CH2:51][C:52]([CH3:55])([NH2:54])[CH3:53])([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Si:43]([O:50][CH2:51][C:52]([NH:54][C:20]([C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=4)[NH:8][N:7]=3)[N:12]=2)[NH:17][CH:18]=1)=[O:21])([CH3:55])[CH3:53])([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 148067402-tert-Butyldimethylsilyloxy-1,1-dimethylethylamineHCID 712798942-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 71280441HCID 71280441, compoundYield 46.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.34 mmol), EDCI (130 mg, 0.68 mmol), DMAP (83 mg, 0.68 mmol) and DIEA (88 mg, 0.68 mmol) in 6 mL of DMF was added 1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-amine (138 mg, 0.68 mmol) in one portion at room temperature, then the mixture was stirred for 16 hours. The reaction mixture was poured into 40 mL of water, filtered and the filter cake was washed with petroleum ether to give crude N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (75 mg, 46.0%) as a pale yellow solid. MS: (M+H)+=479.2.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with petroleum ether

Sources & evidence

ORD record
ord-64adde278a8f418597bff6cb1e4b2078
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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