Trifluoroacetic acid → HCID 86643698, compound

HRID 1672787Notes

Reaction equation

[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([NH:22][NH2:23])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1.C(N(CC)CC)C.[F:35][C:36]([F:41])([F:40])[C:37](O)=[O:38]>ClCCl>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=3)[C:20]([NH:22][NH:23][C:37](=[O:38])[C:36]([F:41])([F:40])[F:35])=[O:21])[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (257 mg, 0.67 mmol) obtained in Step 2 of Example 56 was dissolved in dichloromethane (8.0 mL), and the mixture was cooled to 0° C. after adding triethylamine (0.19 mL, 1.34 mmol). Thereafter, anhydrous trifluoroacetic acid (0.19 mL, 1.34 mmol) was added dropwise to the mixture, and the mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, and a 3 mol/L aqueous sodium hydroxide solution was added to the resulting residue to adjust the pH at 4. The precipitated white solid was then filtered off to obtain (S)-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)-N′-(2,2,2-trifluoroacetyl)benzoic hydrazide (300 mg, 93%).

Workup

concentrationThe mixture was concentrated under reduced pressure
additiona 3 mol/L aqueous sodium hydroxide solution was added to the resulting residue
filtrationThe precipitated white solid was then filtered off

Sources & evidence

ORD record: ord-0d77ee09680d44ebb763013b6e2fe115
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998954B2

Reaction notes

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