Methyl iodide → HCID 59511499, compound

HRID 1157780Notes

Reaction equation

HRID 1157780 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)=[C:5]2[NH:14][CH:15]=[C:16]([C:17](=[O:37])[C:18]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[N:30]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=5)[N:29]=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[O:19])[C:4]=12.[H-].[Na+].[CH3:40]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:13]=[CH:12][N:11]([CH3:40])[N:10]=2)=[C:5]2[NH:14][CH:15]=[C:16]([C:17](=[O:37])[C:18]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[N:30]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=5)[N:29]=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[O:19])[C:4]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178493711HCID 178493711, compound

Product 1

HCID 59511499HCID 59511499, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-methoxy-7-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.069 g, 0.138 mmol) in DMF (3 mL) was added NaH (0.055 g, 1.381 mmol). The mixture was stirred for ten minutes and MeI (0.017 mL, 0.276 mmol) was added. After being stirred for 45 minutes, the mixture was quenched with water. The mixture was concentrated under reduced pressure. The resulting residue was diluted with DMF and was passed through a plug of cotton to remove solids. The DMF solution was purified by prep HPLC to give 1-(4-methoxy-7-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione as a light-yellow solid (0.017 g, 0.033 mmol, 33.1% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 12.37 (s, 1H) 8.67 (dd, J=4.88, 1.22 Hz, 1H) 8.33 (s, 1H) 8.13-8.18 (m, 1H) 8.05 (s, 1H) 7.93 (d, J=2.14 Hz, 1H) 7.85 (d, J=7.93 Hz, 1H) 7.64 (dd, J=7.48, 4.73 Hz, 1H) 6.99 (s, 1H) 4.05 (s, 3H) 4.00 (s, 3H) 3.70-3.74 (m, 2H) 3.40-3.48 (m, 4H) 3.24-3.29 (m, 2H). LCMS: m/e 514.38 (M+H)+, ret time 1.820 min (method 1).

Workup

  1. stirringAfter being stirred for 45 minutes
  2. customthe mixture was quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionThe resulting residue was diluted with DMF
  5. customto remove solids
  6. customThe DMF solution was purified by prep HPLC

Sources & evidence

ORD record
ord-326d0444626e47e390d1cc823cd27f19
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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