Methanol → HCID 136377168, compound

HRID 1027265Notes

Reaction equation

HRID 1027265 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[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.[BH4-].[Na+].CO>C(O)(=O)C>[CH3:29][N:18]([CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]1)[C:15]1[N:14]=[N:13][C:12]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][C:2]=2[OH:1])[CH:8]([OH:11])[CH2:7][CH2:6]3)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 136377167HCID 136377167, compound

Product 1

HCID 136377168HCID 136377168, 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, 50 mg, 0.13 mmol), sodium borohydride (9.59 mg, 0.25 mmol) and MeOH (1.5 mL). The resulting suspension was stirred at RT for two 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+]=397.3, LCMS Rt=0.46 min [LCMS Method Q]; 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.11 (d, J=9.54 Hz, 1H), 7.64 (s, 1H), 7.31 (d, J=9.54 Hz, 1H), 6.99 (s, 1H), 5.16 (t, J=6.53 Hz, 1H), 5.01-5.13 (m, 1H), 2.95-3.08 (m, 4H), 2.73-2.86 (m, 1H), 2.41-2.54 (m, 1H), 1.91 (s, 1H), 1.53-1.78 (m, 4H), 1.41 (s, 6H), 1.26 (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-5f939f12246a4b40847ce693f9966fec
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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