Triethylamine → HCID 88583020, compound

HRID 1508574Notes

Reaction equation

[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[CH:28][C:29]([F:42])=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]([OH:40])=[O:39])=[CH:34][C:33]=5[CH3:41])[CH:31]=4)=[CH:24][N:23]=[C:22](S(C)(=O)=O)[N:21]=3)[C@H:14]2[CH3:47])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[F:51][C:52]1([F:56])[CH2:55][NH:54][CH2:53]1.CCN(CC)CC>C1COCC1>[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[CH:28][C:29]([F:42])=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([C:38]([OH:40])=[O:39])=[CH:34][C:33]=5[CH3:41])[CH:31]=4)=[CH:24][N:23]=[C:22]([N:54]4[CH2:55][C:52]([F:56])([F:51])[CH2:53]4)[N:21]=3)[C@H:14]2[CH3:47])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the title compound from Step D (22 mg, 0.031 mmol), 3,3-difluoro-azetidine hydrochloride (20 mg, 0.155 mmol) and Et3N (31.3 mg, 0.309 mmol) in THF (5 mL) was stirred at 60° C. overnight. The solvent was removed. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.1% TFA, to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 8.34 (s, 1H), 8.08 (s, 1H), 8.02 (d, J=8 Hz, 1H), 7.93 (s, 1H), 7.77 (s, 2H), 7.17-7.42 (m, 4H), 5.72 (d, J=8.0 Hz, 1H), 4.90 (d, J=17 Hz, 1H), 4.55 (m, 4H), 4.40 (m, 1H), 4.08 (d, J=17 Hz, 1H), 2.35 (s, 3H), 0.77 (d, J=7 Hz, 3H). LCMS=725.3 (M+H)+

Workup

customThe solvent was removed
customThe residue was purified by preparative HPLC Reverse phase (C-18)
washeluting with Acetonitrile/Water+0.1% TFA

Sources & evidence

ORD record: ord-f90897fd2bc745f6aab692142e256279
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221834B2

Reaction notes

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