4-Methylmorpholine → HCID 11692434, compound

HRID 548463Notes

Reaction equation

HRID 548463 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][C:12]#[C:13][C:14]([OH:16])=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[N:39]=[CH:38][C:37]([C:43]#[N:44])=[C:36]2[NH:45][C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([Br:52])[CH:47]=1.C([O-])(O)=O.[Na+]>C1COCC1.N1C=CC=CC=1>[Br:52][C:48]1[CH:47]=[C:46]([NH:45][C:36]2[C:35]3[C:40](=[CH:41][CH:42]=[C:33]([NH:32][C:14](=[O:16])[C:13]#[C:12][CH2:11][N:8]4[CH2:7][CH2:6][C:5]5([O:1][CH2:2][CH2:3][O:4]5)[CH2:10][CH2:9]4)[CH:34]=3)[N:39]=[CH:38][C:37]=2[C:43]#[N:44])[CH:51]=[CH:50][CH:49]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 18548944HCID 18548944, compound

Product 1

HCID 11692434HCID 11692434, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of 1.75 g (7.78 mmol) of 4-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)but-2-ynoic acid in 100 mL of THF under N2 was added 0.942 g (9.33 mmol) of N-methylmorpholine followed by 0.852 g (6.22 mmol) of isobutyl chloroformate. After stirring in the cold for 30 min, a solution of 1.05 g (3.11 mmol) of 6-amino-4-[(3-bromophenyl)amino]-quinoline-3-carbonitrile in 8 mL of pyridine was added dropwise. After stirring in the cold for 5 h, the reaction was poured into ice water and satd NaHCO3 was added. The mixture was extracted with ethyl acetate and the extracts were dried and evaporated. Chromatography of the residue on silica gel (20% methanol in ethyl acetate) gave 0.590 g of 4-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)but-2-ynoic acid[4-(3-bromophenylamino)-3-cyanoquinol-6-yl]amide as a brown foam: mass spectrum (electrospray, m/e): M+H 546.0, 548.1.

Workup

  1. stirringAfter stirring in the cold for 5 h
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-35a445c0fe754ebd8b5ebdf6e15e6311
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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