2,2,2-Trifluoroethanesulfonyl chloride → HCID 60142919, compound

HRID 535902Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]([C:28]([NH2:30])=[O:29])=[N:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=4)[CH:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[F:31][C:32]([F:39])([F:38])[CH2:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl.N1C=CC=CC=1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]([C:28]([NH2:30])=[O:29])=[N:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:34]([CH2:33][C:32]([F:39])([F:38])[F:31])(=[O:36])=[O:35])[CH:22]=4)[CH:20]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of EXAMPLE 65A (18 mg, 0.045 mmol) in dichloromethane (0.4 mL) and pyridine (0.1 mL) was added to a cooled to 0° C. 2,2,2-trifluoroethanesulfonyl chloride (9 mg, 0.05 mmol). The reaction mixture was stirred slowly warming to ambient temperature over 18 hours and concentrated under reduced pressure. The crude material was purified by RP-HPLC (10 mM ammonium acetate/acetonitrile) to afford the title compound. 1H NMR (DMSO-d6) δ ppm 10.27 (s, 1H), 8.21 (d, J=3.0, 1H), 8.14 (d, J=1.9, 1H), 7.68-7.63 (m, 1H), 7.52-7.40 (m, 2H), 7.40-7.33 (m, 2H), 7.30-7.23 (m, 1H), 7.20-7.14 (m, 2H), 7.00-6.94 (m, 2H), 4.54 (q, J=9.8, 2H), 3.13 (m, 4H), 2.45 (m, 4H), 2.24 (s, 3H); MS (ESI) m/z 549 (M+H)+.

Workup

temperaturewarming to ambient temperature over 18 hours
concentrationconcentrated under reduced pressure
customThe crude material was purified by RP-HPLC (10 mM ammonium acetate/acetonitrile)

Sources & evidence

ORD record: ord-0b8ebd5596474ac2bac0fdf8c7b027ff
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859546B2

Reaction notes

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