Hydrochloric Acid → HCID 178421997, compound

HRID 1618549Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]3[NH:13][CH2:14][C:15]4([CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:10]3=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1.Cl[C:29]1[C:38]2[C:33](=[CH:34][C:35]([F:39])=[CH:36][CH:37]=2)[N:32]=[C:31]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([O:46]C)[N:41]=2)[C:30]=1[CH3:48]>CN1C(=O)CCC1>[F:39][C:35]1[CH:34]=[C:33]2[C:38]([C:29]([N:13]3[C:11]4[C:10](=[CH:9][CH:8]=[C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)[CH:12]=4)[C:15]4([CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH2:14]3)=[C:30]([CH3:48])[C:31]([C:40]3[N:41]=[C:42]([OH:46])[CH:43]=[CH:44][CH:45]=3)=[N:32]2)=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Prepared according to procedure L using 6-morpholino-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (87 mg, 0.32 mmol) (described herein), 4.0M hydrochloric acid in 1,4-dioxane (66 μL, 0.25 mmol), 4-chloro-7-fluoro-2-(6-methoxypyridin-2-yl)-3-methylquinoline (80 mg, 0.25 mmol) (described herein), and NMP (440 μL), and heating in a microwave at 150° C. for 180 min. Purification afforded 6-(7-fluoro-3-methyl-4-(6-(4-morpholinyl)-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-pyran]-1(2H)-yl)-2-quinolinyl)-2-pyridinol as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.65-7.85 (2H, m), 7.48-7.61 (1H, m), 7.27-7.32 (1H, m), 7.15 (1H, d, J=8.2 Hz), 6.78 (1H, d, J=6.7 Hz), 6.73 (1H, d, J=9.4 Hz), 6.37 (1H, dd, J=8.2, 2.3 Hz), 5.56 (1H, d, J=2.3 Hz), 3.98-4.09 (2H, m), 3.88-3.98 (2H, m), 3.62-3.78 (4H, m), 3.47-3.61 (2H, m), 2.84-3.03 (4H, m), 2.51 (3H, s), 2.09-2.24 (2H, m), 1.83-1.93 (1H, m), 1.71-1.83 (1H, m). Mass Spectrum (ESI) m/e=527 (M+1).

Workup

customPrepared
customPurification

Sources & evidence

ORD record: ord-cff64e43539a43dbab853376268ed74b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

Loading…