Triacetoxyperiodinane → HCID 89717631, compound

HRID 930206Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoro-1-hydroxyethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.200 g, 0.304 mmol) and Dess-Martin periodinane reagent (0.567 g, 1.336 mmol) in DCM (7.50 mL) were stirred at 20° C. for one hour. After evaporation to dryness, the residue was purified by flash chromatography to afford methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoroacetyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (181 mg, 91% yield) as a yellow foam: 1H NMR in DMSO-d6 is consistent with the desired product but complicated due to presence of hydrate form: MS m/z 657.3 (M+H)+; HPLC 96.0% @ 220 nm and 95.3% @ 254 nm, RT 1.87 and 1.96 (ketone+hydrate) minutes.

Workup

customAfter evaporation to dryness
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-3f1c8bac0d9b4ebdb91d361e59f827f1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296744B2

Reaction notes

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