Ethanol → {3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-methyl-carbamic acid 2-morpholin-4-yl-ethyl ester

HRID 1796681Notes

Reaction equation

HRID 1796681 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10](=[O:40])[NH:11][C:12]2[C:13]([CH3:39])=[C:14]3[C:19]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[O:34][CH3:35])=[CH:23][CH:22]=4)=[C:18]([C:36]#[N:37])[CH:17]=[N:16][N:15]3[CH:38]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CI.[H-].[Na+].[CH3:45]CO>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][C:10](=[O:40])[N:11]([C:12]2[C:13]([CH3:39])=[C:14]3[C:19]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[O:34][CH3:35])=[CH:25][CH:26]=4)=[C:18]([C:36]#[N:37])[CH:17]=[N:16][N:15]3[CH:38]=2)[CH3:45])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20791505{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester

Product 1

HCID 21025050{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-methyl-carbamic acid 2-morpholin-4-yl-ethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 432A (27 mg, 0.050 mmol) and CH3I (3.1 μl, 0.05 mmol) in THF (1 ml) was added NaH (1.5 mg, 0.06 mmol). The resulting mixture was stirred at rt for 2 h under argon. A drop of EtOH was added to quench the reaction. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5/30/65 MeOH/EtOAc/CH2Cl2) gave 432 (17.1 mg, 62%) as a yellow oil. It has a retention time of 5.70 min (standard LC1 method, 8 min run). MS Found: (M+H)+=557.1

Workup

  1. customto quench
  2. customthe reaction
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-64d4abb000a8451493995bca83fd0700
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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