Methyl iodide → HCID 89922761, compound

HRID 921919Notes

Reaction equation

HRID 921919 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH:15]3[CH2:19][C:18](=[O:20])[N:17]([CH3:21])[CH2:16]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:22]#[N:23])=[CH:4][C:3]=1[NH:24][C:25]1[N:30]=[C:29]([N:31]([CH:41]2[CH2:43][CH2:42]2)CC2C=CC(OC)=CC=2)[C:28]2=[N:44][CH:45]=[C:46]([C:47]#[N:48])[N:27]2[N:26]=1.IC.[C:51](=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:51])[CH:15]3[CH2:19][C:18](=[O:20])[N:17]([CH3:21])[CH2:16]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:22]#[N:23])=[CH:4][C:3]=1[NH:24][C:25]1[N:30]=[C:29]([NH:31][CH:41]2[CH2:42][CH2:43]2)[C:28]2=[N:44][CH:45]=[C:46]([C:47]#[N:48])[N:27]2[N:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 899231402-((2-Chloro-5-cyano-3-(4-((1-methyl-5-oxopyrrolidin-3-yl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 89922761HCID 89922761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A vial was charged with 2-((2-chloro-5-cyano-3-(4-((1-methyl-5-oxopyrrolidin-3-yl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (35 mg, 0.053 mmol) and iodomethane (3.94 μl, 0.063 mmol) in tetrahydrofuran (263 μl). Cesium carbonate (34.2 mg, 0.105 mmol) was added and the reaction mixture was stirred at room temperature 5 h. The reaction mixture was quenched with water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was used as is in the final deprotection.

Workup

  1. customThe reaction mixture was quenched with water and ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  3. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-296697607e954a0a8ec807a875636929
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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