Phenethylamine → HCID 178523144, compound

HRID 456644Notes

Reaction equation

HRID 456644 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:41]([NH2:49])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH2:41]([NH:49][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[NH:8][CH:7]=1)=[O:5])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178469891HCID 178469891, compound

Product 1

HCID 178523144HCID 178523144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (50 mg, 0.22 mmol) (from Example 11), HOBt (74 mg, 2.5 eq.), EDAC (105 mg, 2.5 eq.), phenethylamine (106 mg, 4 eq.) and TEA (0.5 mL) in DMF (1 mL) was heated at 40° C. for overnight. The reaction was concentrated and purified on a silica gel column to give the titled compound as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-4c02ccdde9c74f538bb90ab2510b6a5e
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

Loading…