5-(3-{5-[(5R)-5-Hydroxymethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenoxy)-N-(4-methoxybenzyl)-N-methylpyridine-2-sulfonamide → 5-(3-{5-[(5R)-5-(Hydroxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenoxy)-N-methylpyridine-2-sulfonamide

HRID 909675Notes

Reaction equation

HRID 909675 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:14]=[C:15]([CH:37]=[C:38]([O:40][C@@H:41]([CH3:45])[CH2:42][O:43][CH3:44])[CH:39]=3)[O:16][C:17]3[CH:18]=[CH:19][C:20]([S:23]([N:26](CC4C=CC(OC)=CC=4)[CH3:27])(=[O:25])=[O:24])=[N:21][CH:22]=3)=[CH:10][CH:9]=2)=[N:5][CH2:4]1>FC(F)(F)C(O)=O>[OH:1][CH2:2][C@@H:3]1[O:7][C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:14]=[C:15]([CH:37]=[C:38]([O:40][C@@H:41]([CH3:45])[CH2:42][O:43][CH3:44])[CH:39]=3)[O:16][C:17]3[CH:18]=[CH:19][C:20]([S:23]([NH:26][CH3:27])(=[O:24])=[O:25])=[N:21][CH:22]=3)=[CH:10][CH:9]=2)=[N:5][CH2:4]1

Participants

3

Reactant 1

HCID 666833095-(3-{5-[(5R)-5-Hydroxymethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenoxy)-N-(4-methoxybenzyl)-N-methylpyridine-2-sulfonamide

Product 1

HCID 666811055-(3-{5-[(5R)-5-(Hydroxymethyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenoxy)-N-methylpyridine-2-sulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-(3-{5-[(5R)-5-Hydroxymethyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}-5-[(1S)-2-methoxy-1-methylethoxy]phenoxy)-N-(4-methoxybenzyl)-N-methylpyridine-2-sulfonamide (292 mg, 0.47 mmol) synthesized in Example (127a) was dissolved in trifluoroacetic acid (2 mL), and stirring was carried out at 45° C. for 6 hours. The solvent was distilled off under reduced pressure, methylene chloride and triethylamine were added in small portions to the residue, and the solvent was distilled off again under reduced pressure. The resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%) to afford the desired compound (184 mg, yield 100%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, methylene chloride and triethylamine
  2. additionwere added in small portions to the residue
  3. distillationthe solvent was distilled off again under reduced pressure
  4. customThe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%)

Sources & evidence

ORD record
ord-97e6d26ff0314cffb9347f6bec46aa3a
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

Loading…