4-Piperidinol, 1-methyl- → HCID 131728133, compound

HRID 2239332Notes

Reaction equation

HRID 2239332 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[S:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[CH:15][C:9]=2[CH:8]=[N:7]1.[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:11]([OH:12])(=[O:36])[CH3:10].[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([O:1][C:2]2[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=2)[CH2:5][N:6]2[C:11](=[O:12])[C:10]3[S:13][C:14]([C:16]4[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=4)=[CH:15][C:9]=3[CH:8]=[N:7]2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 660484-Piperidinol, 1-methyl-HCID 5462977Diethyl azodicarboxylateHCID 68711194HCID 68711194, compound

Product 1

HCID 131728133HCID 131728133, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(3-Hydroxybenzyl)-2-[4-(trifluoromethyl)phenyl]thieno[2,3-d]pyridazin-7(6H)-one (0.203 g, 0.50 mmol), 1-methylpiperidin-4-ol (0.074 g, 0.64 mmol) and TPP (0.172 g, 0.66 mmol) were stirred in THF (3 mL) at 0° C. DEAD (0.3 mL, 40% in toluene, 0.66 mmol) was added and the resulting mixture was allowed to attain room temperature and the stirring continued over night. Concentration and purification on C8-HPLC (0.1% HOAc, gradient 30→40% CH3CN) gave 0.022 g (8%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.19 (s, 1H), 7.77 (d, 2H, J=8.3 Hz), 7.70 (d, 2H, J=8.3 Hz), 7.51 (s, 1H), 7.22 (dd, 1H, J=8.2, 7.7 Hz), 7.04 (d, 1H, J=7.7 Hz), 7.00 (bs, 1H), 6.78 (dd, 1H, J=8.2, 0.9 Hz), 5.37 (s, 2H), 4.44 (br, 1H), 2.88-2.72 (m, 4H), 2.45 (s, 3H), 2.15-2.05 (m, 2H), 1.99 (s, 3H), 1.98-1.88 (m, 2H). MS (ESI+) 500 (M+1H+).

Workup

  1. customto attain room temperature
  2. waitthe stirring continued over night
  3. concentrationConcentration and purification on C8-HPLC (0.1% HOAc, gradient 30→40% CH3CN)

Sources & evidence

ORD record
ord-bb3ed60fe26d457cbabe53114b0a74bf
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

Loading…