Hydrochloric Acid → HCID 44231410, compound

HRID 1259130Notes

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-c1768203b1e6463a8b45c088524feee0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466167B2

Reaction notes

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