Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1802886Notes

Reaction equation

HRID 1802886 reaction equation
[CH:1]1([S:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:16]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:17](=[O:20])[CH:18]=[CH2:19])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH:28][CH:29]([C:34]1[CH:35]=[CH:36][C:37]([CH:40]=[O:41])=[N:38][CH:39]=1)[C:30]([OH:33])([CH3:32])[CH3:31].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH:1]1([S:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:16]([CH2:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:17](=[O:20])[CH2:18][CH2:19][C:40]([C:37]2[CH:36]=[CH:35][C:34]([CH:29]([OH:28])[C:30]([OH:33])([CH3:31])[CH3:32])=[CH:39][N:38]=2)=[O:41])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 583806064-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde

Product 1

HCID 583806055-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 71%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.80 g), 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (0.99 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (0.12 g), triethylamine (0.26 ml), tetrahydrofuran (10 mL) and ethanol (10 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography to give the title compound (1.90 g, yield 71%) as a yellow amorphous solid from the fraction eluted with ethyl acetate. MS: 584 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7220a97cc6d74572b55b74b2748bbace
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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