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 2285304Notes

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-8be42b38f8e146e093d92b9c6524ce5f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145413B2

Reaction notes

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