Triethylamine → HCID 68767893, compound

HRID 1455462Notes

Reaction equation

HRID 1455462 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([O:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C@H:8]2[CH2:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[C:3]1=[O:24].C(N(CC)CC)C.Cl[C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:43]([F:46])([F:45])[F:44])[CH:41]=2)[N:36]=[CH:35][N:34]=1>CCO>[CH:14]([O:13][C@@H:10]1[CH2:11][CH2:12][C@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[C:40]([C:43]([F:45])([F:46])[F:44])[CH:41]=4)[N:36]=[CH:35][N:34]=3)[C:3]2=[O:24])[C@H:8]([CH2:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:9]1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 68768989HCID 68768989, compound

Product 1

HCID 68767893HCID 68767893, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-3-amino-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonylmethyl)cyclohexyl)pyrrolidin-2-one (0.04 g, 0.128 mMol), triethylamine (71 uL, 0.512 mMol) and 4-chloro-6-(trifluoromethyl)quinazoline (0.035 g, 0.192 mMol) were taken in EtOH and microwaved at 100° C. for 45 min. The reaction mixture was concentrated and chromatographed to yield (S)-1-((1S,2R,4R)-4-isopropoxy-2-(isopropylsulfonyl methyl)cyclohexyl)-3-(6-(trifluoro methyl)quinazolin-4-ylamino)pyrrolidin-2-one as a white solid (0.04 g). MS found: (M+H)+=557.2

Workup

  1. custommicrowaved at 100° C. for 45 min
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed

Sources & evidence

ORD record
ord-5660b156ede54b599f26bc716d102f8b
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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