Triacetoxyperiodinane → 1-[5-tert-Butyl-2-(4-formyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea

HRID 2282763Notes

Reaction equation

HRID 2282763 reaction equation
ClCCl.[C:4]([C:8]1[CH:9]=[C:10]([NH:21][C:22]([NH:24][C@@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:28]([O:35][C:36]3[CH:37]=[CH:38][C:39]4[N:40]([C:42]([N:45]5[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]5[CH3:51])=[N:43][N:44]=4)[CH:41]=3)[CH2:27][CH2:26]2)=[O:23])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)[N:12]=1)([CH3:7])([CH3:6])[CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:4]([C:8]1[CH:9]=[C:10]([NH:21][C:22]([NH:24][C@@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:28]([O:35][C:36]3[CH:37]=[CH:38][C:39]4[N:40]([C:42]([N:45]5[CH2:50][CH2:49][CH2:48][CH2:47][C@@H:46]5[CH3:51])=[N:43][N:44]=4)[CH:41]=3)[CH2:27][CH2:26]2)=[O:23])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)[N:12]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 866873151-[5-tert-Butyl-2-(4-hydroxymethyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea dichloromethane

Product 1

HCID 866873141-[5-tert-Butyl-2-(4-formyl-phenyl)-2H-pyrazol-3-yl]-3-{(1S,4R)-4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-ureaYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Intermediate 176a (1.10 g, 1.70 mmol) in DCM (25 mL) at 0° C. was added Dess-Martin periodinane (791 mg, 1.86 mmol) and the resulting red-brown solution stirred at 0° C. for 45 min. Sodium metabisulfite (920 mg), water (10 mL) and sat. aq. NaHCO3 solution (10 mL) were added and the mixture stirred at RT until gas evolution ceased (15 min). The mixture was diluted with water (25 mL) and extracted with DCM (2×25 mL). The combined organics were passed through a hydrophobic fit and concentrated in vacuo to leave the title compound as a glassy orange solid (1.10 g, 100%). LCMS (Method 3): Rt 3.91 min, m/z 647 [MH+].

Workup

  1. stirringthe mixture stirred at RT until gas evolution
  2. custom(15 min)
  3. extractionextracted with DCM (2×25 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a19feabf1e0b44088bd696df107e414f
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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