1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58094808, compound

HRID 2282327Notes

Reaction equation

HRID 2282327 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:15][C:14]([C:16](O)=[O:17])=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.CC[N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>CCOC(C)=O.O.CN(C=O)C.C(N(CC)CC)C>[CH3:1][C:2]1[C:10]([C:11]2[S:15][C:14]([C:16]([NH2:27])=[O:17])=[C:13]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 58094953HCID 58094953, compound

Product 1

HCID 58094808HCID 58094808, compoundYield 72.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-3-phenylthiophene-2-carboxylic acid (100 mg, 0.299 mmol), EDCI (450 mg, 2.35 mmol), HOBt (95 mg, 0.703 mmol), triethylamine (2.5 mL), ammonium chloride (870 mg, 16.3 mmol) and DMF (35 mL) was stirred for 16 h at rt. To the mixture, were added water and EtOAc and the resulting biphasic mixture was vigorously stirred for 30 min. The organic phase was washed with water and brine and then 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 to yield the title compound (72 mg, 71%) as a pale yellow solid. 1H NMR (300 MHz, d6-DMSO) δ: 8.68 (d, J=7.0 Hz, 1H), 7.92 (d, J=9.1 Hz, 1H), 7.70-7.53 (m, 2H), 7.53-7.31 (m, 4H), 7.26 (s, 1H), 7.11-6.71 (m, 3H), 2.59 (s, 3H).

Workup

  1. stirringthe resulting biphasic mixture was vigorously stirred for 30 min
  2. washThe organic phase 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

Sources & evidence

ORD record
ord-0c858da559b240e496c30baec1456c6c
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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