Sodium Hydroxide → HCID 67325374, compound

HRID 1028948Notes

Reaction equation

N=[C:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([NH2:20])[C:14]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[CH:13]2.[OH-:35].[Na+]>Cl>[NH2:20][C:15]1[C:14]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:4]3[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[O:35])[CH:11]=2)[N:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 6-(2-(imino(2-methoxyphenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine (0.022 g, 0.049 mmol) in 5N aq. HCl (2 mL) was heated to 100° C. in a sealed tube for 16 h, then allowed to cool to 50° C. and heated for another 70 h at that temperature. The mixture was neutralized with 10N NaOH and filtered. The precipitate was redissolved in MeOH and purified by reverse-phase HPLC (10-90% acetonitrile/H2O, TFA modifier). A single fraction was treated with NH4OH and the acetonitrile was removed in vacuo. The resulting suspension was filtered and air-dried to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(2-methoxyphenyl)methanone. MS (ESI, pos. ion) m/z: 454 (M+1).

Workup

temperatureheated for another 70 h at that temperature
filtrationfiltered
dissolutionThe precipitate was redissolved in MeOH
custompurified by reverse-phase HPLC (10-90% acetonitrile/H2O, TFA modifier)
additionA single fraction was treated with NH4OH
customthe acetonitrile was removed in vacuo
filtrationThe resulting suspension was filtered
customair-dried

Sources & evidence

ORD record: ord-89aa22b3b34e404d9a46e3dd5cea61a5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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