Triethylamine → HCID 117771438, compound

HRID 2201546Notes

Reaction equation

HRID 2201546 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:41](O)=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[F:75][C:76]1[CH:81]=[CH:80][C:79]([CH2:82][NH2:83])=[CH:78][CH:77]=1>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[C:10]([C:41]([NH:83][CH2:82][C:79]2[CH:80]=[CH:81][C:76]([F:75])=[CH:77][CH:78]=2)=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117771339HCID 117771339, compound

Product 1

HCID 117771438HCID 117771438, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinic acid (200 mg, 0.33 mmol), HATU (252 mg, 0.66 mmol) and Et3N (111 mg, 1 mmol) was stirred in DMF (5 mL) at RT for 1 h, and then (4-fluorophenyl)methanamine (124 mg, 1 mmol) was added. After being stirred for 3 h, the mixture was diluted with water and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography (DCM:MeOH=100:1 to 50:1) to get the product of 3-(benzyloxy)-N-(4-fluorobenzyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinamide (225 mg, yield: 96%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.90˜7.94 (m, 2H), 7.83 (s, 1H), 7.76 (s, 1H), 7.65˜7.72 (m, 2H), 7.43˜7.45 (m, 2H), 7.28˜7.34 (m, 5H), 7.22 (t, J=8.6 Hz, 2H), 6.91 (t, J=8.6 Hz, 2H), 5.20 (s, 2H), 4.50 (s, 2H), 3.14 (s, 3H), 2.89 (s, 3H), 2.87 (s, 3H). MS (M+H)+: 711.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. custompurified by column chromatography (DCM:MeOH=100:1 to 50:1)

Sources & evidence

ORD record
ord-3b7f5fe9ab1b443192480186e1756ed1
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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