Triethylamine → {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

HRID 1796680Notes

Reaction equation

HRID 1796680 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10](C(O)=O)[C:11]([CH3:12])=[C:5]2[C:4]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])=[CH:19][CH:18]=1)#[N:2].CC[N:34](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[N:56]1(CCO)[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1.[CH3:65][CH2:66][O:67][C:68](C)=[O:69]>O1CCOCC1>[N:56]1([CH2:65][CH2:66][O:67][C:68](=[O:69])[NH:34][C:10]2[C:11]([CH3:12])=[C:5]3[C:4]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[O:30][CH3:31])=[CH:19][CH:18]=4)=[C:3]([C:1]#[N:2])[CH:8]=[N:7][N:6]3[CH:9]=2)[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 611632-MorpholinoethanolHCID 199401P,P-Diphenylphosphinic azideHCID 221796673-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid

Product 1

HCID 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 esterYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 430D (41 mg, 0.10 mmol), Et3N (56 μl, 0.40 mmol) and DPPA (43 μl, 0.20 mmol) in dioxane (1 ml) was stirred at rt for 2 h under argon, 2-morpholin-4-yl-ethanol (49 μl, 0.40 mmol) was added. The resulting mixture was heated to 80° C. for 2 h, cooled to rt. Treated with EtOAc (20 ml), the mixture was washed with H2O (2×5 ml) and brine (10 ml), dried with Na2SO4. Removal of the solvent followed by flash chromatography of the residue on silica gel (3%-5% MeOH—CH2Cl2) gave 432A (47 mg, 88%) as a light yellow solid. It has a retention time of 5.35 min (∠Cl, 8 min. run). MS Found: (M+H)+=543.2

Workup

  1. temperatureThe resulting mixture was heated to 80° C. for 2 h
  2. temperaturecooled to rt
  3. washthe mixture was washed with H2O (2×5 ml) and brine (10 ml)
  4. dry with materialdried with Na2SO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-5bce7a130fe446f3b67b52ac26443857
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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