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 631002Notes

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

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

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

Sources & evidence

ORD record: ord-a3c400670add4274882c606a7a4e3e26
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315503B2

Reaction notes

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