Tetrahydrofuran → HCID 24804444, compound

HRID 2094214Notes

Reaction equation

HRID 2094214 reaction equation
C(OC([C:6]1[N:10]([CH:11]([CH3:13])[CH3:12])[C:9]([C:14]2[C:19]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:18][C:17]([Cl:34])=[CH:16][N:15]=2)=[N:8][N:7]=1)=O)C.[CH3:35][Mg]Br.[CH2:38]1[CH2:42][O:41]CC1>>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([S:21]([NH:20][C:19]2[C:14]([C:9]3[N:10]([CH:11]([CH3:13])[CH3:12])[C:6]([C:42]([OH:41])([CH3:38])[CH3:35])=[N:7][N:8]=3)=[N:15][CH:16]=[C:17]([Cl:34])[CH:18]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24803941HCID 24803941, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24804444HCID 24804444, compound

Conditions

Temperature
0 °C

Procedure

A 25 mL scintillation vial was charged with 5-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-4-isopropyl-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester (prepared according to general procedure B, 11 mg, 0.02 mmol), methylmagnesium bromide in THF (0.2 mL, 3.0 M), and tetrahydrofuran (3 mL). The vial was sealed and stirred at 0° C. for 2 h. The volatiles were then evacuated in vacuo and the residue was purified via preparatory HPLC to afford 4-tert-butyl-N-{5-chloro-2-[5-(1-hydroxy-1-methyl-ethyl)-4-isopropyl-4H-[1,2,4]triazol-3-yl]-pyridin-3-yl}-benzenesulfonamide as a white powder: MS (ES) M+H expected 492.2. found 492.5.

Workup

  1. customThe vial was sealed
  2. customThe volatiles were then evacuated in vacuo
  3. customthe residue was purified via preparatory HPLC

Sources & evidence

ORD record
ord-08fc69e0d8f44387b2c3fa0ac01d4072
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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