Methyl iodide → HCID 178480071, compound

HRID 81183Notes

Reaction equation

HRID 81183 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].IC.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]3[N:20]([CH2:30][C@H:31]4[CH2:36][CH2:35][C@H:34]([CH3:37])[CH2:33][CH2:32]4)[C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH:24]4[C:28]#[CH:29])=[N:22][C:18]=3[CH:17]=[C:16]([C:38]3[NH:42][C:41](=[O:43])[O:40][N:39]=3)[N:15]=2)[CH:11]=[N:12][CH:13]=1.[CH3:44]CN(C(C)C)C(C)C>[Cu]I.CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:19]3[N:20]([CH2:30][C@H:31]4[CH2:32][CH2:33][C@H:34]([CH3:37])[CH2:35][CH2:36]4)[C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH:24]4[C:28]4[N:1]=[N:2][N:3]([CH3:44])[CH:29]=4)=[N:22][C:18]=3[CH:17]=[C:16]([C:38]3[NH:42][C:41](=[O:43])[O:40][N:39]=3)[N:15]=2)[CH:11]=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 178436505HCID 178436505, compound

Product 1

HCID 178480071HCID 178480071, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a reaction vessel were added DMSO (0.4 mL), sodium azide (0.005 g, 0.080 mmol) and iodomethane (0.006 mL, 0.085 mmol). The reaction vessel was sealed and stirred at 50° C. for 12 hours. To the reaction was then added 3-(4-(5-chloropyridin-3-yl)-2-(2-ethynylpyrrolidin-1-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (0.020 g, 0.039 mmol), CuI (0.004 g, 0.019 mmol), and DIEA (0.015 mL, 0.086 mmol). The reaction vessel was sealed and further stirred at 50° C. for 6 hours. To the reaction was added DMSO (0.6 mL), and the solution was passed through a syringe filter. The filtrate was purified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water: 0.1% v/v TFA modifier) to afford 3-(4-(5-chloropyridin-3-yl)-2-(2-(1-methyl-1H-1,2,3-triazol-4-yl)pyrrolidin-1-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (TFA salt). MS ESI calc'd. for C28H31ClN10O2 [M+H]+ 575. found 575. 1H NMR (500 MHz, DMSO-d6): δ 12.81 (s, 1H); 8.85 (s, 1H); 8.77 (d, J=2.3 Hz, 1H); 8.41 (s, 1H); 7.94 (s, 1H); 7.79 (s, 1H); 5.50 (t, J=7.1 Hz, 1H); 3.94 (s, 3H); 3.80-3.86 (m, 3H); 3.43-3.46 (m, 1H); 2.37-2.39 (m, 1H); 2.12-2.18 (m, 2H); 1.95-2.00 (m, 1H); 1.28-1.30 (m, 2H); 0.96-1.03 (m, 2H); 0.66 (d, J=6.5 Hz, 4H); 0.41-0.44 (m, 3H); 0.30-0.36 (m, 2H).

Workup

  1. customThe reaction vessel was sealed
  2. customThe reaction vessel was sealed
  3. stirringfurther stirred at 50° C. for 6 hours
  4. customthe solution was passed through a syringe
  5. filtrationfilter
  6. customThe filtrate was purified by reverse phase preparative HPLC (0:100 to 95:5 acetonitrile:water: 0.1% v/v TFA modifier)

Sources & evidence

ORD record
ord-4b326c9b7ee9476abda41fd8d989a4ef
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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