Trifluoroacetic acid → HCID 71469258, compound

HRID 1529176Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[N:13][C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[N:17](COCC[Si](C)(C)C)[C:15]=4[N:16]=3)=[N:9][N:8]([CH2:31][CH2:32][C:33]([F:38])([F:37])[CH:34]([F:36])[F:35])[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[N:13][C:14]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=4[N:16]=3)=[N:9][N:8]([CH2:31][CH2:32][C:33]([F:38])([F:37])[CH:34]([F:35])[F:36])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

96 mg (0.173 mmol) of the compound from Example 37A were stirred in dichloromethane (4 ml) and trifluoroacetic acid (1 ml) at room temperature for 4.5 h. The mixture was then concentrated to dryness. The residue was stirred in ethanol/2N hydrochloric acid (4:1, 15 ml) at 45° C. for 3 h. This was followed by concentration to dryness. Purification by preparative HPLC (methanol:water (+1% trifluoroacetic acid) gradient) gave 31 mg of the title compound (42% of theory).

Workup

concentrationThe mixture was then concentrated to dryness
concentrationThis was followed by concentration to dryness
customPurification by preparative HPLC (methanol:water (+1% trifluoroacetic acid) gradient)

Sources & evidence

ORD record: ord-4dfa2aae8ae64fd880cb83ea5620d9ab
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090610B2

Reaction notes

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