Isopropanol → Isopropyl 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]-1,3-thiazole-4-carboxylate

HRID 1986458Notes

Reaction equation

HRID 1986458 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27]1[S:28][CH:29]=[C:30]([C:32]([OH:34])=[O:33])[N:31]=1)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:39](O)([CH3:41])[CH3:40].C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27]1[S:28][CH:29]=[C:30]([C:32]([O:34][CH:39]([CH3:41])[CH3:40])=[O:33])[N:31]=1)=[CH:15][CH:14]=2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 688291742-[3-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]-1,3-thiazole-4-carboxylic acid

Product 1

HCID 68832561Isopropyl 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]-1,3-thiazole-4-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]-1,3-thiazole-4-carboxylic acid (0.26 g, 0.5 mmol), n-tributylphosphine (0.25 ml, 1.0 mmol), isopropanol (0.5 ml) and tetrahydrofuran (10 ml) was added 1,1-(azodicarbonyl)dipiperidine (0.25 g, 1.0 mmol), and the mixture was stirred at room temperature for 2 hrs. Precipitated crystals were removed and the solvent was evaporated. The residue was purified by silica gel column chromatography to give isopropyl 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]-1,3-thiazole-4-carboxylate (0.20 g, yield 71%) as white crystals.

Workup

  1. customPrecipitated crystals
  2. customwere removed
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f02f6231e1f047989560445ddf61da91
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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