Sodium Hydroxide → HCID 178434227, compound

HRID 2189167Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)/[CH:13]=[CH:14]/[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[CH3:24])[CH:2]([CH3:4])[CH3:3].N1([CH2:35][C:36]([NH2:38])=[O:37])C2C=CC=CC=2N=N1.[OH-].[Na+]>CCO>[CH3:24][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([C:14]3[CH:13]=[C:12]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[NH:38][C:36](=[O:37])[CH:35]=3)[CH:16]=2)[NH:20][N:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of (E)-1-(2-isobutoxyphenyl)-3-(3-methyl-1H-indazol-5-yl)prop-2-en-1-one (50 mg, 0.15 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamide (Aldrich) (50 mg, 2.84 mmol), and 20 mg of NaOH in 10 mL of EtOH was heated to 90° C. for 4 h. The reaction mixture was concentrated down and purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate) to afford 4-(3-methyl-1H-indazol-5-yl)-6-{2-[(2-methylpropyl)oxy]phenyl}pyridin-2(1H)-one (12 mg, 21.4%). 1H NMR (400 MHz, d6-DMSO): δ 12.78 (s, 1H), 8.15 (s, 1H), 7.71 (d, 1H), 7.53 (m, 2H), 7.45 (t, 1H), 7.15 (d, 1H), 7.07 (t, 1H), 6.77 (br s, 1H), 6.61 (s, 1H), 3.84 (d, 2H), 2.02 (m, 1H), 0.95 (d, 6H); MS (EI) for C23H23N3O2: 374 (MH+).

Workup

concentrationThe reaction mixture was concentrated down
custompurified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate)

Sources & evidence

ORD record: ord-49142bdd7db4423cb84e77909b59f6c3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324231B2

Reaction notes

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