Triethylamine → HCID 86603548, compound

HRID 408518Notes

Reaction equation

HRID 408518 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]2[S:14][C:13]([NH2:15])=[N:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.CO[C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]([OH:29])=O)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1([O:53][C:54](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]2[S:14][C:13]([NH:15][C:27]([C:24]3([C:21]4[CH:20]=[CH:19][CH:18]=[C:23]([O:53][CH3:54])[CH:22]=4)[CH2:25][CH2:26]3)=[O:29])=[N:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60027522HCID 60027522, compound

Product 1

HCID 86603548HCID 86603548, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

5-(2-Methoxy-pyridin-3-ylmethyl)-thiazol-2-ylamine (221 mg, 1.00 mmol) and 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (192 g, 1.00 mmol) were dissolved in acetonitrile (5 mL) containing triethylamine (0.421 mL, 3.00 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 760 mg, 2.0 mmol) was added and the solution was allowed to stir at 78° C. for 12 hours. An aliquot of the crude product was purified by reverse-phase preparative liquid chromatography. ESI-MS m/z calc. 395.1. found; 396.3 (M+1)+ Retention time 3.27 minutes.

Workup

  1. customAn aliquot of the crude product was purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-3aee0bdcb67143d48d32eee46c5f8bde
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

Loading…