Iodine → HCID 89717942, compound

HRID 930210Notes

Reaction equation

HRID 930210 reaction equation
II.[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:50])[CH2:15][CH2:16][CH2:17][NH:18][C:19]1[C:31]2[C:30]3[C:25](=[CH:26][C:27]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=3)[NH:24][C:23]=2[N:22]=[C:21]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3([C:46]([F:49])([F:48])[F:47])[NH:45][NH:44]3)[CH:38]=2)[N:20]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C>C(Cl)Cl>[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:50])[CH2:15][CH2:16][CH2:17][NH:18][C:19]1[C:31]2[C:30]3[C:25](=[CH:26][C:27]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=3)[NH:24][C:23]=2[N:22]=[C:21]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3([C:46]([F:47])([F:48])[F:49])[N:44]=[N:45]3)[CH:38]=2)[N:20]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 89717640HCID 89717640, compound

Product 1

HCID 89717942HCID 89717942, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Iodine (27.8 mg, 0.110 mmol) was added to a 5 mL round-bottomed flask protected from light and pre-charged with methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(3-(trifluoromethyl)diaziridin-3-yl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (70 mg, 0.104 mmol) and triethylamine (43.6 μL, 0.313 mmol) in DCM (2 mL) to give a light yellow solution. After stirring at 20° C. for 15 minutes, the solvent was evaporated and the residue purified by flash chromatography to give methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (65 mg, 0.097 mmol, 93% yield) as a light yellow foam: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 1.53 (dt, J=13.8, 7.0 Hz, 2H) 1.70-1.82 (m, 2H) 2.15 (br. s., 3H) 2.24-2.34 (m, 2H) 2.34-2.42 (m, 2H) 2.87-2.98 (m, 2H) 3.55-3.66 (m, 2H) 3.88 (s, 3H) 4.10 (s, 2H) 6.76 (br. s., 1H) 7.14 (d, J=8.2 Hz, 1H) 7.27 (s, 1H) 7.43 (t, J=7.8 Hz, 1H) 7.49-7.58 (m, 2H) 7.83 (dd, J=8.2, 1.4 Hz, 1H) 7.99 (d, J=1.4 Hz, 1H) 8.27 (d, J=8.2 Hz, 1H) 12.06 (s, 1H); MS m/z 669.2 (M+H)+; HPLC 97.6% @ 220 nm and 97.3% @ 254 nm, RT=2.18 minutes.

Workup

  1. customto give a light yellow solution
  2. customthe solvent was evaporated
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-582c6a0b8d6347eb9c52559db372a1d4
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

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