Methanol → HCID 136377165, compound

HRID 1027264Notes

Reaction equation

HRID 1027264 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][C:3]=1[C:12]1[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)=[CH:16][CH:17]=1.[ClH:30].[NH2:31][OH:32].N1C=CC=CC=1.CO>C(O)(=O)C>[ClH:30].[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[N:31][OH:32])=[CH:4][C:3]=1[C:12]1[N:13]=[N:14][C:15]([N:18]([CH3:29])[CH:19]2[CH2:20][C:21]([CH3:28])([CH3:27])[NH:22][C:23]([CH3:25])([CH3:26])[CH2:24]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 136377167HCID 136377167, compound

Product 1

HCID 136377165HCID 136377165, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a microwave vial was added 6-hydroxy-5-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-2,3-dihydro-1H-inden-1-one (Example 35-1,150 mg, 0.38 mmol), hydroxylamine hydrochloride (264 mg, 3.80 mmol), pyridine (0.25 mL, 3.04 mmol) and MeOH (1.0 mL). The resulting suspension was stirred at RT for 1.5 hours. The reaction mixture was acidified with excess acetic acid and loaded onto an SCX column. The crude material was washed with methanol then eluted with 2 N ammonia in methanol. The product-containing fractions were concentrated to afford the title compound. MS [M+H+]=410.2, LCMS Rt=0.48 min [Method Q]; 1H NMR (400 MHz, DMSO-d6) ppm 10.94-11.13 (m, 1H), 8.91-9.21 (m, 1H), 8.29 (d, J=10.04 Hz, 1H), 8.09-8.21 (m, 1H), 7.83 (s, 1H), 7.52-7.73 (m, 1H), 7.08 (s, 1H), 4.83-5.31 (m, 1H), 2.91-3.04 (m, 5H), 2.74-2.85 (m, 2H), 1.91-2.09 (m, 2H), 1.79 (d, J=10.79 Hz, 2H), 1.53 (s, 6H), 1.47 (s, 6H).

Workup

  1. washThe crude material was washed with methanol
  2. washthen eluted with 2 N ammonia in methanol
  3. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-ddf5243656c74ae190d65df498f08387
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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