Trifluoroacetic acid → HCID 18400071, compound

HRID 1888343Notes

Reaction equation

C(O)(C(F)(F)F)=O.C([NH:12][S:13]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]3[C:33]([CH:34]=[O:35])=[C:32]([Cl:36])[N:31]=[C:30]3[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:24][CH:23]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14])(C)(C)C>>[CH2:37]([C:30]1[N:29]([CH2:28][C:25]2[CH:26]=[CH:27][C:22]([C:17]3[C:16]([S:13]([NH2:12])(=[O:14])=[O:15])=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:23][CH:24]=2)[C:33]([CH:34]=[O:35])=[C:32]([Cl:36])[N:31]=1)[CH2:38][CH2:39][CH3:40]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57931404HCID 57931404, compound

Product 1

HCID 18400071HCID 18400071, compound

Conditions

Temperature: 80 °C

Procedure

C2HF3O2 (1b): TFA (10 mL, 129.8 mmol) was added to intermediate (1a) (5.0 g, 10.2 mmol). The mixture was stirred at 80° C. for 2 hours. TFA was removed under vacuum and the crude intermediate (1b), as a TFA salt, was used in the next step (5.6 g). Anal. HPLC: retention time=3.4 minutes. Gradient conditions: 25% solvent B/75% solvent A to 95% solvent B/5% solvent B over 6 minutes. MS m/z: [M+H]+ calcd for C21H22ClN3O3S, 432.11. found 432.2.

Workup

customTFA was removed under vacuum
waitGradient conditions: 25% solvent B/75% solvent A to 95% solvent B/5% solvent B over 6 minutes

Sources & evidence

ORD record: ord-21e02034832848aeb4e7b478cbfc76cb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501798B2

Reaction notes

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