Triethylamine → HCID 117771043, compound

HRID 2201532Notes

Reaction equation

HRID 2201532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]([OH:35])=O)[C:30]([O:36][CH3:37])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.[F:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][NH2:46])=[N:43][CH:44]=1.CCN(CC)CC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]([NH:46][CH2:45][C:42]5[CH:41]=[CH:40][C:39]([F:38])=[CH:44][N:43]=5)=[O:35])[C:30]([O:36][CH3:37])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 45079543(5-Fluoropyridin-2-yl)methanamineHCID 117771171HCID 117771171, compound

Product 1

HCID 117771043HCID 117771043, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-methoxypicolinic acid (50 mg, 0.09 mmol), (5-fluoropyridin-2-yl)methanamine (200 mg, 1.58 mmol) and Et3N (0.2 mL) in THF (50 mL) was added T3P (0.05 mL) dropwise at 0° C. and the mixture was stirred for 3 h. After being diluted with water and extracted with EtOAc, the combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by prep-TLC (PE:EtOAc=1:2) to give the pure product of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-N-((5-fluoropyridin-2-yl)methyl)-3-methoxypicolinamide (20 mg, yield: 30%). 1H-NMR (CDCl3, 400 MHz) δ 8.60 (t, J=4.8 Hz, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.99 (s, 1H), 7.92˜7.95 (m, 2H), 7.73 (d, J=8.4 Hz, 1H), 7.58 (s, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.24˜7.42 (m, 2H), 7.17˜7.22 (m, 2H), 5.91 (d, J=3.6 Hz, 1H), 4.73 (d, J=5.6 Hz, 2H), 4.01 (s, 3H), 3.18 (s, 3H), 2.97 (d, J=4.8 Hz, 3H), 2.78 (s, 3H). MS (M+H)+: 636.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by prep-TLC (PE:EtOAc=1:2)

Sources & evidence

ORD record
ord-8d79b4d523e24ab3931539267439f607
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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