Triacetoxyperiodinane → HCID 71714973, compound

HRID 930197Notes

Reaction equation

CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1([CH2:29][CH2:30][CH2:31][NH:32][C:33]2[C:45]3[C:44]4[C:39](=[CH:40][C:41]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:43]=4)[NH:38][C:37]=3[N:36]=[C:35]([CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([CH:57]([OH:62])[C:58]([F:61])([F:60])[F:59])[CH:52]=3)[N:34]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[N:23]1([CH2:29][CH2:30][CH2:31][NH:32][C:33]2[C:45]3[C:44]4[C:39](=[CH:40][C:41]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:43]=4)[NH:38][C:37]=3[N:36]=[C:35]([CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([C:57](=[O:62])[C:58]([F:59])([F:61])[F:60])[CH:52]=3)[N:34]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 20 °C

Procedure

Dess-Martin periodinane (56.5 mg, 0.133 mmol) was added to methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(2,2,2-trifluoro-1-hydroxyethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (20 mg, 0.036 mmol) in DCM (753 μL) to give a white suspension. After stirring at 20° C. for 1 hour the mixture was purified by flash chromatography to give methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(2,2,2-trifluoroacetyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate as Example 33 (18.4 mg, 92% yield) as a yellow solid: 1H NMR in DMSO-d6 was consistent with the desired product but complicated because of the presence of hydrate forms; HRMS m/z 554.2384 (M+H)+; HPLC >95%, RT=1.76 and 1.87 minutes (ketone+hydrate).

Workup

customto give a white suspension
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-2cce7a8c97a14ff086d86651ce4105ee
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296744B2

Reaction notes

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