Triethylamine → HCID 20747308, compound

HRID 970914Notes

Reaction equation

HRID 970914 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:39]=[CH:40][CH:41]=1)[CH2:17][N:18]([CH2:29][C:30]1[NH:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[N:31]=1)[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1.CCN(CC)CC>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[CH2:29][N:18]([CH2:17][C:16]1[CH:15]=[C:14]([CH:41]=[CH:40][CH:39]=1)[CH2:13][NH:12][C:4](=[O:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[N:10][C:2]=1[CH3:1])[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 9887073HCID 9887073, compound

Product 1

HCID 20747308HCID 20747308, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2,4-dimethyl-nicotinic acid (56 mg, 0.37 mmol) in SOCl2 (˜3 mL, excess) was heated to 80° C. for 4 hours. The condenser was removed and the mixture was flushed with N2 at 80° C. for ˜5 minutes and then dried in vacuo for 10 minutes. The resulting syrup was dissolved in CH2Cl2 (2.0 mL) and added to a stirring mixture of (3-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (147 mg, 0.37 mmol), Et3N (0.26 mL, 1.85 mmol) and a catalytic amount of DMAP. The reaction mixture was stirred ovemight at room temperature. Purification of the crude yellow foam by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:1:1) followed by radial chromatography on silica gel (1 mm plate, EtOAc/MeOH/NH4OH, 200:1:1) afforded the desired amide (85 mg, 43%) as a light yellow foam.

Workup

  1. customThe condenser was removed
  2. customthe mixture was flushed with N2 at 80° C. for ˜5 minutes
  3. customdried in vacuo for 10 minutes
  4. dissolutionThe resulting syrup was dissolved in CH2Cl2 (2.0 mL)
  5. customPurification of the crude yellow foam by column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 100:1:1)

Sources & evidence

ORD record
ord-e7edc77f52624170a97b1e468e8dc5ee
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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