Diisopropylethylamine → HCID 86618150, compound

HRID 2246580Notes

Reaction equation

HRID 2246580 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH2:16])[C:12]2=[O:17])[CH2:9][CH2:8][C@@H:7]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:6]1)(=[O:3])[CH3:2].Cl[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:37]([F:40])([F:39])[F:38])[CH:35]=2)[N:30]=[CH:29][N:28]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[C:1]([NH:4][C@H:5]1[C@@H:10]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[C:34]([C:37]([F:39])([F:40])[F:38])[CH:35]=4)[N:30]=[CH:29][N:28]=3)[C:12]2=[O:17])[CH2:9][CH2:8][C@@H:7]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 86618149HCID 86618149, compound

Product 1

HCID 86618150HCID 86618150, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-3-amino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (˜3.4 mmol) in isopropanol (10 mL) was added 4-chloro-6-(trifluoromethyl)quinazoline (0.97 g, 1.2 eq) and diisopropylethylamine (0.88 g, 2 eq). The mixture was stirred at room temperature for 2.5 h. The solvent was removed under reduced pressure. The residue was purified with silica gel column chromatography eluting with 1% and 5% MeOH in dichloromethane to provide tert-butyl (1R,3R,4S)-3-acetamido-4-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexylcarbamate (2.0 g, ˜100%). LC/MS found [M+H]+=551.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified with silica gel column chromatography
  3. washeluting with 1% and 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-a7360e6253f44fee87960c355bab04ce
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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