Dichloromethane → HCID 71714955, compound

HRID 930193Notes

Reaction equation

HRID 930193 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:25]1[N:26]=[C:27]([NH:42][CH2:43][CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[C:28]2[C:36]3[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=3)[NH:30][C:29]=2[N:41]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[C:24]([C:25]1[N:26]=[C:27]([NH:42][CH2:43][CH2:44][CH2:45][N:46]2[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]2)[C:28]2[C:36]3[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=3)[NH:30][C:29]=2[N:41]=1)(=[O:23])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 71714956HCID 71714956, compound

Product 1

HCID 71714955HCID 71714955, compoundYield 79%

Procedure

Dess-Martin periodinane reagent (22.67 mg, 0.053 mmol) was added to a mixture of methyl 2-(hydroxy(phenyl)methyl)-4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (compound of Example 22) and TFA (15.7 mg, 0.027 mmol) in DCM (1000 μL, 15.54 mmol) to give a light orange solution. After 1 h, the solvent was evaporated and the residue was purified by flash chromatography to afford Example 23: methyl 2-benzoyl-4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (10 mg, 79% yield) as a bright yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27-1.36 (m, 2H) 1.36-1.48 (m, 4H) 1.74-1.88 (m, 2H) 2.14-2.44 (m, 6H) 3.52-3.68 (m, 2H) 3.91 (s, 3H) 7.54 (t, J=7.8 Hz, 2H) 7.69 (t, J=7.4 Hz, 1H) 7.76 (t, J=5.1 Hz, 1H) 7.90 (dd, J=8.2, 1.4 Hz, 1H) 7.94 (d, J=7.0 Hz, 2H) 8.10 (d, J=1.4 Hz, 1H) 8.52 (d, J=8.2 Hz, 1H) 12.43 (s, 1H); HRMS m/z 472.2342 (M+H)+; HPLC 97.1% @ 220 nm and 98.9% @ 254 nm, RT=1.86 minutes.

Workup

  1. customto give a light orange solution
  2. customthe solvent was evaporated
  3. customthe residue was purified by flash chromatography
  4. customto afford Example 23

Sources & evidence

ORD record
ord-6f70d24138c145e787c4e524f66732fe
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

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