Methyl iodide → HCID 178430231, compound

HRID 2205243Notes

Reaction equation

HRID 2205243 reaction equation
[CH3:1][C:2]1[C:3]2[S:10][C:9]([C:11]3[N:15]4[N:16]=[C:17]([NH:20][C@H:21]5[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:30]I>CN(C=O)C>[CH3:30][N:20]([C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1)[C:17]1[CH:18]=[CH:19][C:14]2[N:15]([C:11]([C:9]3[S:10][C:3]4[C:2]([CH3:1])=[CH:7][N:6]=[CH:5][C:4]=4[CH:8]=3)=[CH:12][N:13]=2)[N:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178430232HCID 178430232, compound

Product 1

HCID 178430231HCID 178430231, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-4-(3-(7-methylthieno[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol (37 mg, 0.0975 mmol, 1.0 equiv) in DMF (2.00 mL) was added sodium hydride (20 mg, 0.488 mmol, 5.0 equiv) and methyl iodide (68 mg, 0.488 mmol, 5.0 equiv). After 2 h, the reaction mixture was quenched with water and extracted with ethyl acetate. Purification by column chromatography gave 20 mg (50%) of N-((1r,4r)-4-methoxycyclohexyl)-N-methyl-3-(7-methylthieno[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-amine as the less polar product and 10 mg (25%) of trans-4-(N-methyl-N-(3-(7-methylthieno[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanol as the more polar product.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-b6927ab0505d42278d82dfb53fcfa1cd
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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