Sulfur trioxide-pyridine → HCID 44200056, compound

HRID 1254789Notes

Reaction equation

HRID 1254789 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][C@@H:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:19][N:20]=2)[C@@H:13]([OH:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[O-].[Na+:30].N1C=CC=CC=1.[S:37](=[O:40])(=[O:39])=[O:38]>C1COCC1>[S:37]([O-:40])([O:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[O:17][C:16]([C@H:12]([NH:11][C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=3[CH3:10])[C@@H:13]([OH:15])[CH3:14])=[N:20][N:19]=2)=[CH:26][CH:25]=1)(=[O:39])=[O:38].[Na+:30]

Participants

5

Reactant 3

HCID 168533Sulfur trioxide-pyridineHCID 10942334Sodium MethoxideHCID 135870878HCID 135870878, compound

Product 1

HCID 44200056HCID 44200056, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-4-((1R,2S)-2-hydroxy-1-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)propylamino)-3-methylbenzonitrile (example 8) (257 mg, 0.67 mmol) in THF (2.0 mL) was added a solution of sodium methoxide (36 mg, 0.67 mmol) in THF (1.5 mL) at room temperature. After 20 minutes sulfur trioxide-pyridine (85 mg, 0.53 mmol) was added and the mixture was stirred for 40 minutes, then partitioned between H2O (25 mL) and Et2O (20 mL). The aqueous layer was concentrated under reduced pressure to provide a colourless solid (177 mg, 68%): 1H NMR (400 MHz, d6-DMSO, δ in ppm) 7.88 (dm, J=9.0 Hz, 2H), 7.56 (d, J=8.6 Hz, 1H), 7.36 (dm, J=8.8 Hz, 2H), 6.80 (d, J=8.8 Hz, 1H), 5.86 (d, J=8.6 Hz, 1H), 5.49 (d, J=6.1 Hz, 1H), 5.08 (dd, J=4.3, 8.4 Hz, 1H), 4.40 (tq, J=3.9, 5.9 Hz, 1H), 2.33 (s, 3H), 1.25 (d, J=6.3 Hz, 3H).

Workup

  1. custompartitioned between H2O (25 mL) and Et2O (20 mL)
  2. concentrationThe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09ace8f7a22d487ab65d924e774d448e
Source dataset
uspto-grants-2013_06
Patent number
US08455525B2

Reaction notes

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