Triethylamine → HCID 55043537, compound

HRID 2201557Notes

Reaction equation

HRID 2201557 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[NH2:10][C:11]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][C:12]=1[C:13](O)=[O:14].CCN(CC)CC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl.O>[NH2:10][C:11]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][C:12]=1[C:13]([NH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 111923Propylphosphonic anhydrideHCID 7374452-Amino-5-bromonicotinic acid

Product 1

HCID 55043537HCID 55043537, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a degassed solution of (4-fluorophenyl)methanamine (500 mg, 4.0 mmol), 2-amino-5-bromonicotinic acid (867 mg, 4.0 mmol) and Et3N (1.21 g, 12.0 mmol) in dry DCM (10 mL) was added T3P (2.54 g, 8.0 mmol) at 0° C. under N2 protection. The mixture was stirred at 0° C. for 20 minutes. The mixture was diluted with water, and then it was extracted with EtOAc, dried over Na2SO4, filtrated and concentrated to give the crude product of 2-amino-5-bromo-N-(4-fluorobenzyl)nicotinamide (1.05 g, yield: 81%). 1H-NMR (CDCl3, 400 MHz) δ 8.18 (s, 1H), 7.64 (d, J=2.0 Hz, 1H), 7.31 (t, J=8.0 Hz, 2H), 7.05 (d, J=8.8 Hz, 2H), 6.38 (d, J=4.0 Hz, 2H), 6.17 (d, J=5.2 Hz, 1H), 5.12 (d, J=6.4 Hz, 2H). MS (M+H)+: 324/326.

Workup

  1. extractionit was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-acbb028704624741b62c6a48f86f7b92
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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