Sodium Hydroxide → HCID 90356936, compound

HRID 55887Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 44 (1 g, 3.25 mmol) in toluene was heated to 50° C. and Red-Al (2.2 mL, 8.14 mmol) was introduced at 50° C. After the addition was complete, the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was cooled to rt, basified with 1N aq. NaOH solution and extracted with 10% MeOH/CHCl3. The combined organic layer was dried over Na2SO4, concentrated and the obtained crude compound was purified by silica gel chromatography (100-200 mesh, eluted with 2% MeOH/DCM) to get compound 45 (300 mg, 33%) as gummy liquid; (m/z): 294 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 9.76 (1H, s), 8.24 (1H, d, J=5.6 Hz), 7.53 (1H, d, J=1.2 Hz), 7.30 (1H, d, J=2.0, 5.6 Hz), 3.58 (4H, t, J=4.6 Hz), 3.48 (2H, s), 2.40-2.38 (4H, m), 1.49 (9H, s).

Workup

additionAfter the addition
temperatureThe reaction mixture was cooled to rt
extractionextracted with 10% MeOH/CHCl3
dry with materialThe combined organic layer was dried over Na2SO4
concentrationconcentrated
customthe obtained crude compound
customwas purified by silica gel chromatography (100-200 mesh, eluted with 2% MeOH/DCM)

Sources & evidence

ORD record: ord-36c51dda74604ab2b33b4f26705754f5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09433622B2

Reaction notes

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