1,1,1-Trifluoro-2-iodoethane → HCID 71534973, compound

HRID 2175141Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([S:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][C:21]([N:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[CH:20]5)=[N:14][N:15]=3)[CH:12]=2)[CH:4]=[N:3]1.[F:33][C:34]([F:38])([F:37])[CH2:35]I.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([S:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][C:21]([N:27]4[CH2:32][CH2:31][N:30]([CH2:35][C:34]([F:38])([F:37])[F:33])[CH2:29][CH2:28]4)=[CH:20]5)=[N:14][N:15]=3)[CH:12]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 6-(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)-3-(piperazin-1-yl)quinoline (Example 27—see in Table below) (12 mg, 0.027 mmol), 1,1,1-trifluoro-2-iodoethane (56.9 mg, 0.271 mmol) and DIPEA (17.5 mg, 0.136 mmol) in DMF (1 mL) was sealed in a microwave vial and heated at 120° C. for 6 hours. The solvent was removed and the residue was purified by prep-HPLC to give the title compound as yellow solid (3 mg, yield 20%). [Method 1C]

Workup

customwas sealed in a microwave vial
customThe solvent was removed
customthe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-a021db1bbb1b40dc82eec87ecaa1f40c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062045B2

Reaction notes

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