1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178433764, compound

HRID 2282226Notes

Reaction equation

HRID 2282226 reaction equation
Cl.Cl.[CH3:3][C:4]1[C:16]([C:17]2[S:18][C:19]([C:28]3[N:32]=[CH:31][NH:30][N:29]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)=[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][NH2:15])[CH:10]=[CH:11][N:6]2[N:5]=1.[CH3:33][N:34]1[CH:38]=[C:37]([C:39](O)=[O:40])[N:36]=[CH:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CCOC(C)=O.O.CN(C=O)C>[CH3:33][N:34]1[CH:38]=[C:37]([C:39]([NH:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][N:6]3[N:5]=[C:4]([CH3:3])[C:16]([C:17]4[S:18][C:19]([C:28]5[N:32]=[CH:31][NH:30][N:29]=5)=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:7]3[CH:8]=2)=[O:40])[N:36]=[CH:35]1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178433763HCID 178433763, compound

Product 1

HCID 178433764HCID 178433764, compoundYield 29.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-({2-methyl-3-[4-phenyl-5-(1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridin-5-yl}oxy)ethanamine di-hydrochloride (100 mg, 0.20 mmol) obtained in Example 73-B(i), TEA (1.5 mL), 1-methyl-1H-imidazole-4-carboxylic acid (120 mg, 0.95 mmol), HOBT (220 mg, 1.6 mmol), EDCI (350 mg, 1.8 mmol) and DMF (10 mL) was stirred at rt for 14 h. To the reaction mixture were added water (200 mL) and EtOAc (200 mL) and the mixture was stirred for 30 min. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was washed with EtOAc and diisopropyl ether, and dried to give the title compound (31 mg, 29%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe residue was washed with EtOAc and diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-b2f96d7d21c84672b8b91c3c550f1caf
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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