1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71288483, compound

HRID 246711Notes

Reaction equation

HRID 246711 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](O)=[O:22])=[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.CCN(C(C)C)C(C)C.[NH2:44][C:45]1([CH2:48][NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[CH2:47][CH2:46]1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[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]([NH:44][C:45]5([CH2:48][NH:49][C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])[CH2:47][CH2:46]5)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 68451901tert-Butyl [(1-aminocyclopropyl)methyl]carbamateHCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 71288483HCID 71288483, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 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 (0.10 g, 0.32 mmol), EDCI (0.123 g, 0.64 mmol), DMAP (0.122 g, 1 mmol) and DIPEA (0.11 g, 0.90 mmol) in 6 mL of DMF was added tert-butyl (1-aminocyclopropyl)methylcarbamate (0.20 g, 1.07 mmol) in one portion at room temperature and stirred for 16 hours. The mixture was poured into 50 mL of water, and filtered. The filter cake was washed with water, dried and used in the next step without further purification. MS: (M+H)+=480.2.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water
  3. customdried
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-b57eca5440524bafaf957aa8dca7f11d
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…