Triethylamine → HCID 86598508, compound

HRID 32130Notes

Reaction equation

HRID 32130 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)(=[O:29])=[O:28])[CH2:9][C:10]([NH:12][CH:13]2[CH2:22][CH2:21][CH2:20][C:19]3[N:18]=[C:17]([CH2:23][CH2:24][OH:25])[N:16]=[CH:15][C:14]2=3)=[O:11])=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:38])[F:39])[CH:31]=2)(=[O:29])=[O:28])[CH2:9][C:10]([NH:12][CH:13]2[CH2:22][CH2:21][CH2:20][C:19]3[N:18]=[C:17]([CH2:23][CH2:24][O:25][S:41]([CH3:40])(=[O:43])=[O:42])[N:16]=[CH:15][C:14]2=3)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 689308143-(4-fluorophenyl)-N-[2-(2-hydroxy-ethyl)-5,6,7,8-tetrahydro-quinazolin-5-yl]-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

Product 1

HCID 86598508HCID 86598508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluorophenyl)-N-[2-(2-hydroxy-ethyl)-5,6,7,8-tetrahydro-quinazolin-5-yl]-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (56.6 mg, 0.1 mmol) in dry CH2Cl2 at 0 C was added MsCl (34 mg, 0.3 mmol), followed by Et3N (50 mg, 0.5 mmol). After stirring at 0° C. for 20 min, the reaction was quenched with Sat. NaHCO3 solution, extracted with EtOAc, dried over Na2SO4, and evaporated in vacuo. Flash chromatography (SiO2, EtOAc/MeOH=100:3 to 100:5 to 100:7) gave the title compound as a white solid. MS: 645.0 (M+1).

Workup

  1. customthe reaction was quenched with Sat. NaHCO3 solution
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f790801935524f0aa5675e0181297385
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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