Hydrochloric Acid → 3-{[(Benzyloxy)carbonyl]amino}-7-morpholin-4-ylquinoline-2-carboxylic acid

HRID 924441Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:28]([O:30]CC)=[O:29])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:28]([OH:30])=[O:29])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of ethyl 3-{[(benzyloxy)carbonyl]amino}-7-morpholin-4-ylquinoline-2-carboxylate (0.065 g, 0.15 mmol) in 1,4-dioxane (2.0 mL) was added 2.5 M aq. NaOH (1.0 mL, 2.5 mmol). The reaction mixture was heated at 80° C. for 0.5 h, then cooled and neutralized with 2.5 mL 1 M HCl to pH=7. The precipitated solid was collected by filtration and air-dried overnight to yield the sub-title compound (0.042 g, 69%). LCMS (ESI) calc. for C22H22N3O5 [M+H]+: m/z=408.2. found: 408.2.

Workup

temperaturecooled
filtrationThe precipitated solid was collected by filtration
customair-dried overnight

Sources & evidence

ORD record: ord-7d348c33c7144eaeb8a2200c2ad38095
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278950B2

Reaction notes

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