1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18445442, compound

HRID 460353

Reaction equation

HRID 460353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:8]1[NH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:7]=1[CH2:6]2.[O:25]=[C:26]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:27][C:28](O)=[O:29].CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:19][C:15]1[CH:14]=[C:13]([NH:12][C:11]2[C:7]3[CH2:6][C:5]4[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=4)[C:8]=3[N:9]([C:28](=[O:29])[CH2:27][C:26]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:25])[N:10]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9797370Jnj-101984092×HCID 11457817HCID 11457817, compound2×HCID 178526939HCID 178526939, compound

Product 1

HCID 18445442HCID 18445442, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (0.36, 1.0 mmol), 3-Oxo-3-pyrrolidin-1-yl-propionic acid (Compound 28a) (0.157 g, 1.0 mmole), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (0.24 g, 1.25 mmol), hydroxybenzo-triazole hydrate (HOBT) (0.17 g, 1.25 mmol) and DIEA (0.220 mL, 1.25 mmol) was stirred in 10 mL DMF over night at room temperature. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The solvent was removed in vacuo and the crude material was prepped on the Gilson. Lyophilization produced a white powder. MS m/z 465.1 (M+H)+;

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. customThe solvent was removed in vacuo
  4. customLyophilization produced a white powder

Sources & evidence

ORD record
ord-4b01c6e74ab24ec187001f869a5729f2
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Linked notes

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