Ethylamine → HCID 42603288, compound

HRID 450518Notes

Reaction equation

HRID 450518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=3)[C:22]([OH:24])=O)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:28]([NH2:30])[CH3:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[C:21]([C:22]([NH:30][CH2:28][CH3:29])=[O:24])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42603325HCID 42603325, compound

Product 1

HCID 42603288HCID 42603288, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]benzoic acid (Example 63) (0.143 g, 0.35 mmol), ethylamine in THF, 2M solution (1.75 mL, 0.35 mmol), HATU (0.199 g, 0.52 mmol) and DIPEA (0.09 mL, 0.52 mmol) in DMF was stirred at 40° C. for 1 week. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulphate, filtered and concentrated. The title compound was obtained after recrystallisation from acetonitrile as white solid (49 mg, 32%). HRMS calculated for C20H19Cl2N5O2 (M+H)+432.0994, found: 432.0957, Rt: 2.82 min. MP: 192.2° C.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95f9c08be7a8403baeaaaa6625efd63d
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

Loading…