Methyl iodide → HCID 58406344, compound

HRID 1910904Notes

Reaction equation

HRID 1910904 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[N:32]([C:33]([C:35]4[C:36]([CH3:40])=[N:37][O:38][CH:39]=4)=[O:34])[CH2:31][CH2:30][N:16]2[C:17](=[O:29])[C:18]2[N:19]([CH:21]=[C:22]([C:24]4[NH:28][N:27]=[N:26][N:25]=4)[CH:23]=2)[CH2:20]3)=[CH:11][CH:10]=1.CI>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]23[N:32]([C:33]([C:35]4[C:36]([CH3:40])=[N:37][O:38][CH:39]=4)=[O:34])[CH2:31][CH2:30][N:16]2[C:17](=[O:29])[C:18]2[N:19]([CH:21]=[C:22]([C:24]4[N:25]([CH3:1])[N:26]=[N:27][N:28]=4)[CH:23]=2)[CH2:20]3)=[CH:13][CH:14]=1.[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]23[N:32]([C:33]([C:35]4[C:36]([CH3:40])=[N:37][O:38][CH:39]=4)=[O:34])[CH2:31][CH2:30][N:16]2[C:17](=[O:29])[C:18]2[N:19]([CH:21]=[C:22]([C:24]4[N:25]=[N:26][N:27]([CH3:1])[N:28]=4)[CH:23]=2)[CH2:20]3)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178488306HCID 178488306, compound

Product 2

HCID 53371601HCID 53371601, compoundYield 28%HCID 58406344HCID 58406344, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2 equivalents) was added to a solution of 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(1H-tetrazol-5-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (75) (150 mg, 0.33 mmol) in DMF. The mixture was stirred for 10 minutes and methyl iodide was added. The reaction was stirred at room temperature for 1 hour. The crude material was purified by preparative HPLC to give 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(1-methyl-1H-tetrazol-5-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (145) as a white solid (45 mg, 29%) and 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(2-methyl-2H-tetrazol-5-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (146) as a white solid (43 mg, 28%).

Workup

  1. stirringThe reaction was stirred at room temperature for 1 hour
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-871b7dd2025044a2aa0106ee9ea69a9b
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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