1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71280017, compound

HRID 246624Notes

Reaction equation

HRID 246624 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](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.Cl.[NH2:25][C:26]([CH3:30])([CH3:29])[C:27]#[N:28].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.CN(C=O)C>[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]([NH:25][C:26]([C:27]#[N:28])([CH3:30])[CH3:29])=[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 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 122394652-amino-2-methylpropanenitrile hydrochlorideHCID 712800962-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 71280017HCID 71280017, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.07 g, 0.3 mmol), 2-amino-2-methylpropanenitrile hydrochloride (0.05 g, 0.42 mmol), EDCI (0.057 g, 0.3 mmol), DMAP (0.037 g, 0.3 mmol), and DIPEA (0.163 g, 1.26 mmol) in 10 mL of DMF were stirred at room temperature for 5 hours. Then HATU (0.114 g, 0.3 mmol) was added, the final reaction mixture was stirred for additional 15 hours. The solvent was removed under reduced pressure at 70° C., then the residue was triturated with water and ethyl acetate successively then decanted and dried to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(2-cyanopropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.026 g, 31%) as a white solid.

Workup

  1. customthe final reaction mixture
  2. stirringwas stirred for additional 15 hours
  3. customThe solvent was removed under reduced pressure at 70° C.
  4. customthe residue was triturated with water and ethyl acetate successively
  5. customdecanted
  6. customdried

Sources & evidence

ORD record
ord-dd40738205114787aea8fe436c9475ca
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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