2,4,6-Trimethylpyridine → HCID 59559975, compound

HRID 1643703Notes

Reaction equation

HRID 1643703 reaction equation
N1C(C)=CC(C)=CC=1C.[CH3:10][N:11]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[CH:29]=[C:28]([O:30][C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=3)[C:22]3[CH2:23][CH:24]([CH2:26]O)[O:25][C:21]=3[CH:20]=2)=[O:18])=[N:12]1.CCN(S(F)(F)[F:47])CC>C(Cl)Cl>[CH3:10][N:11]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[CH:29]=[C:28]([O:30][C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=3)[C:22]3[CH2:23][CH:24]([CH2:26][F:47])[O:25][C:21]=3[CH:20]=2)=[O:18])=[N:12]1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 123472(Diethylamino)sulfur trifluorideHCID 59560399HCID 59560399, compound

Product 1

HCID 59559975HCID 59559975, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,4,6-collidine (0.0311 mL, 0.235 mmol) and 2-hydroxymethyl-4-(4-methanesulfonyl-phenoxy)-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (200) (50 mg, 0.11 mmol) in CH2Cl2 (3 mL) was cooled to −15° C. DAST (0.0307 mL, 0.235 mmol) was added drop wise. The mixture was stirred at −15° C. to room temperature overnight, then quenched with MeOH at 0° C., concentrated, and purified by column chromatography eluting with 25-75% EtOAc in hexanes to give a white solid (9 mg, 18% yield). 1H NMR (400 MHz, CDCl3) δ 8.48 (s, 1 H) 7.78-8.03 (m, 2 H) 7.20-7.34 (m, 2 H) 7.02-7.20 (m, 3 H) 6.77 (d, J=2.27 Hz, 1 H) 5.01-5.19 (m, 1 H) 4.42-4.78 (m, 2 H) 3.79 (s, 3H) 3.25 (dd, J=16.55, 9.73 Hz, 1 H) 3.08 (s, 3 H) 2.99-3.06 (m, 1 H); LCMS for C21H20FN3O5S m/z 446.00 (M+H+).

Workup

  1. customquenched with MeOH at 0° C.
  2. concentrationconcentrated
  3. custompurified by column chromatography
  4. washeluting with 25-75% EtOAc in hexanes

Sources & evidence

ORD record
ord-5a7c6f8141954155806404912e376847
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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