Hydrochloric Acid → HCID 44231410, compound

HRID 340262Notes

Reaction equation

C([O:3]/[CH:4]=[CH:5]\[C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[C:13]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:12]1=[N:11][C:10]=2[NH2:21])C.Cl.C([O-])(O)=O.[Na+].[Li+].[B-](CC)(CC)CC.C1COCC1>O1CCOCC1>[NH2:21][C:10]1[C:9]2[N:8]=[CH:7][C:6]([CH2:5][CH2:4][OH:3])=[CH:15][C:14]=2[C:13]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:12]=2[N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (Z)-2-(2-ethoxyvinyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (from the previous step) in a mixture of 2:5 conc. HCl and dioxane (0.1 M) was heated at 60° C. overnight. Upon cooling down to rt, the reaction mixture was treated with excess NaHCO3 saturated solution, followed by extraction with EtOAc. Combined organic extracts were concentrated and was taken up in THF (0.2 M), and was treated with 1 N super hydride solution in THF (10 eq.) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was worked up following the procedures described for Example 42/Step 3, to afford 2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethanol as white solid. 1H NMR (CDCl3): δ 8.61 (d, 1H), 8.47 (d, 1H), 8.01 (d, 1H), 7.41 (s, 1H), 7.10 (d, 1H), 6.40 (s, 1H), 6.01 (bs, 2H), 4.01 (t, 2H), 3.06 (t, 2H), 2.43 (s, 3H). LRMS [M+H]=254.1

Workup

temperatureUpon cooling down to rt
extractionfollowed by extraction with EtOAc
concentrationCombined organic extracts were concentrated
temperatureto warm to room temperature

Sources & evidence

ORD record: ord-6eac3f6ab0604586a22a64f7d5ca5bf5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895577B2

Reaction notes

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