Methylamine → HCID 67352455, compound

HRID 1424784Notes

Reaction equation

HRID 1424784 reaction equation
[CH:1]1([C:4]2[C:5]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=4)=[C:9]([C:19](O)=[O:20])[C:8]=3[CH:22]=2)[CH2:3][CH2:2]1.C[CH2:29][N:30](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C1COCC1>CN(C=O)C.O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[O:11][C:7]3[CH:6]=[C:5]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:4]([CH:1]4[CH2:2][CH2:3]4)=[CH:22][C:8]=3[C:9]=2[C:19]([NH:30][CH3:29])=[O:20])=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67353505HCID 67353505, compound

Product 1

HCID 67352455HCID 67352455, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-cyclopropyl-2-(4-chlorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (5 g, 11.52 mmol) in dry DMF (30 mL) was added DIPEA (3.3 g, 25.34 mmol) and HATU (5.15 g, 13.5 mmol) at 20° C. After 15 minutes, 2M Methylamine in THF (23.04 mL, 46.08 mmol) was added dropwise and the mixture was stirred for another 2 hours before water (60 mL) was added. The mixture was extracted with EA (3×200 mL), washed with water (2×200 mL), dried and concentrated to afford 2-(4-Chlorophenyl)-5-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide as a brown solid (4.7 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.32 (br. s., 1H) 8.45 (q, 1H) 7.90 (d, 2H) 7.53-7.64 (m, 3H) 7.16 (s, 1H) 3.06 (s, 3H) 2.83 (d, 3H) 2.21-2.37 (m, 1H) 0.94-1.05 (m, 2H) 0.64-0.73 (m, 2H). LCMS (m/z, ES+)=419 (M+H+).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EA (3×200 mL)
  3. washwashed with water (2×200 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aafc0011f936473f9bbd1612819a0326
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

Loading…