Trifluoroacetic acid → HCID 118692894, compound

HRID 59663Notes

Reaction equation

HRID 59663 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[CH2:31][CH2:32][O:33]C(=O)C)=[C:5]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>>[OH:33][CH2:32][CH2:31][N:10]1[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[S:37]([CH3:40])(=[O:39])=[O:38])[C:18]2[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=2[N:12]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=2)[C:11]1=[O:30]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118692925Acetic acid 2-[4-(4-cyano-2-methanesulfonyl-phenyl)-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-2H-quinazolin-3-yl]-ethyl ester

Product 1

HCID 118692894HCID 118692894, compound

Procedure

Acetic acid 2-[4-(4-cyano-2-methanesulfonyl-phenyl)-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-2H-quinazolin-3-yl]-ethyl ester (step 1, 60.0 mg, 0.10 mmol) is stirred with trifluoroacetic acid (3.0 mL, 36.94 mmol) at 60° C. for 6 h and concentrated under reduced pressure. The residue is stirred over night with acetonitrile and water (→hydrolysis of trifluoroacetic acid ester) and then purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 31.3 mg; ESI mass spectrum [M+H]+=534; Retention time HPLC: 0.78 min (005_CA01).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  3. custom0.78 min (005_CA01)

Sources & evidence

ORD record
ord-a6f3907009474bb4b4d591d923729a9c
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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