Hydrochloric Acid → HCID 90412050, compound

HRID 1522025Notes

Reaction equation

[C:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([F:21])[C:10]=2[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])[N:5](COCC[Si](C)(C)C)[C:4]=1[C:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH:31]=1)#[N:2].Cl>O1CCCC1>[F:21][C:9]1[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[C:11]2[C:3]([C:1]#[N:2])=[C:4]([C:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH:31]=3)[NH:5][C:6]2=[N:7][CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of Example 263F (0.42 g, 0.7 mmol) in tetrahydrofuran (10 mL) was added 35% hydrochloric acid (6 mL) and the mixture was heated at 65° C. overnight. Concentration and purification by HPLC (Zorbax C-18, using a 0-100% gradient of water/acetonitrile, containing 0.1% trifluoroacetic acid) afforded the title compound. 1H NMR (400 MHz, Methanol-d4) δ 3.00 (tq, J=6.2, 2.3 Hz, 2H), 3.58 (td, J=6.5, 2.8 Hz, 2H), 3.77 (s, 3H), 3.77 (s, 3H), 3.98 (q, J=2.7 Hz, 2H), 6.68 (tt, J=3.5, 1.7 Hz, 1H), 7.06-7.17 (m, 2H) 7.19-7.29 (m, 1H), 8.35 (d, J=2.3 Hz, 1H). MS (ESI+) m/z 367 (M+H)+.

Workup

concentrationConcentration and purification by HPLC (Zorbax C-18
additioncontaining 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-750af15afea94a09ad9a6dd6588affa8
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073922B2

Reaction notes

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