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

HRID 1964716Notes

Reaction equation

HRID 1964716 reaction equation
COC1C=CC([CH2:7][N:8](C)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[C:23]([C:25]4[NH:26][C:27]([C:30]5[O:31][C@@H:32]([CH3:35])[CH2:33][N:34]=5)=[CH:28][CH:29]=4)[CH:22]=[C:21]([O:36][C@@H:37]([CH3:41])[CH2:38][O:39][CH3:40])[CH:20]=3)=[CH:14][N:13]=2)(=[O:11])=[O:10])=CC=1>FC(F)(F)C(O)=O>[CH3:40][O:39][CH2:38][C@H:37]([CH3:41])[O:36][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]2[NH:26][C:27]([C:30]3[O:31][C@@H:32]([CH3:35])[CH2:33][N:34]=3)=[CH:28][CH:29]=2)[CH:22]=1)[O:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][CH3:7])(=[O:11])=[O:10])=[N:13][CH:14]=1

Participants

3

Reactant 1

HCID 66681054N-(4-Methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide

Product 1

HCID 666832525-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(4-Methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide (292 mg, 0.47 mmol) synthesized in Example (121c) was dissolved in trifluoroacetic acid (2 mL), and stirring was carried out at 45° C. for 1 hour. 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 (208 mg, yield 88%) 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-7a4632eceb61496381f25039b9179e9c
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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