HCID 86710633, compound → HCID 136377158, compound

HRID 1027227Notes

Reaction equation

HRID 1027227 reaction equation
C([O:8][C:9]1[C:10]([C:26]2[N:31]=[N:30][C:29]([N:32]([CH3:43])[CH:33]3[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]3)=[CH:28][CH:27]=2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[CH:14][CH:13]=2)C1C=CC=CC=1>CO.CCOC(C)=O.[Pd]>[CH3:43][N:32]([CH:33]1[CH2:34][C:35]([CH3:42])([CH3:41])[NH:36][C:37]([CH3:40])([CH3:39])[CH2:38]1)[C:29]1[N:30]=[N:31][C:26]([C:10]2[C:9]([OH:8])=[CH:18][C:17]3[C:12]([CH:11]=2)=[CH:13][CH:14]=[C:15]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH:16]=3)=[CH:27][CH:28]=1

Participants

5

Reactant 1

HCID 86710633HCID 86710633, compound

Product 1

HCID 136377158HCID 136377158, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A H2 purged mixture of 6-(3-(benzyloxy)-6-(piperidin-1-ylmethyl)naphthalen-2-yl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (34 mg, 0.059 mmol) and 10% wt Pd/C (0.3 mg, 3 μmol) in MeOH (3 mL) and EtOAc (3 mL) was stirred under a H2 atmosphere at RT overnight. The reaction mixture was filtered through celite, rinsed with MeOH and concentrated. The crude material was purified via HPLC to give the desired product as a yellow solid (15 mg, 52.3% yield). LCMS Rt=0.45 min [Method Q], MS (M−1)=486.4. 1H NMR (METHANOL-d4) δ 8.16 (s, 1H), 8.12 (d, J=10.1 Hz, 1H), 7.69 (d, J=8.6 Hz, 1H), 7.46 (s, 1H), 7.15-7.22 (m, 2H), 7.14 (s, 1H), 4.98 (t, J=12.1 Hz, 1H), 3.49 (s, 2H), 2.89 (s, 3H), 2.37 (br. s., 4H), 1.34-1.60 (m, 10H), 1.29 (s, 6H), 1.13 (s, 6H).

Workup

  1. customA H2 purged
  2. filtrationThe reaction mixture was filtered through celite
  3. washrinsed with MeOH
  4. concentrationconcentrated
  5. customThe crude material was purified via HPLC

Sources & evidence

ORD record
ord-5171440cf56648b39d23a0845abbdff8
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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