1,2-Dichloroethane → 3-(4-fluorophenyl)-N-[2-(2-hydroxy-ethyl)-5,6,7,8-tetrahydro-quinazolin-5-yl]-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

HRID 32129Notes

Reaction equation

HRID 32129 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[NH2:27][CH:28]1[CH2:37][CH2:36][CH2:35][C:34]2[N:33]=[C:32]([CH2:38][CH2:39][OH:40])[N:31]=[CH:30][C:29]1=2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][C:10]([NH:27][CH:28]2[CH2:37][CH2:36][CH2:35][C:34]3[N:33]=[C:32]([CH2:38][CH2:39][OH:40])[N:31]=[CH:30][C:29]2=3)=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 454662383-(4-Fluorophenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acidHCID 588413542-(5-Amino-5,6,7,8-tetrahydroquinazolin-2-yl)ethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-fluorophenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid (172 mg, 0.44 mmol), crude 2-(5-amino-5,6,7,8-tetrahydro-quinazolin-2-yl)-ethanol (Step G, 85 mg, 0.44 mmol), HOBt (65.5 mg, 0.484 mmol) and EDC (93 mg, 0.484 mmol) in 1.5 mL of DMF was stirred overnight at RT. After quenching with Sat. NaHCO3 solution, the mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vacuo. Flash chromatography (SiO2, EtOAc/MeOH=100:5 to 100:10 to 100:12) gave the title compound as a white solid. MS: 567.0 (M+1).

Workup

  1. customAfter quenching with Sat. NaHCO3 solution
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb5644b263724e8989d7312cfd61bc33
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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