4-Methylmorpholine → HCID 10206633, compound

HRID 612020Notes

Reaction equation

HRID 612020 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[O:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]#[C:24][C:25]([OH:27])=O)[CH2:18][CH2:17]1.[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[C:32]2[NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([Br:48])[CH:43]=1>O1CCCC1.N1C=CC=CC=1>[Br:48][C:44]1[CH:43]=[C:42]([NH:41][C:32]2[C:31]3[C:36](=[CH:37][CH:38]=[C:29]([NH:28][C:25](=[O:27])[C:24]#[C:23][CH2:22][N:19]4[CH2:18][CH2:17][O:16][CH2:21][CH2:20]4)[CH:30]=3)[N:35]=[CH:34][C:33]=2[C:39]#[N:40])[CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5419084-Morpholinotetrolic acidHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 10206633HCID 10206633, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate(0.161 g, 1.18 mmol) and N-methylmorpholine(0.150 g, 1.48 mmol) were added to an ice cold solution of 0.250 g (1.48 mmol) of 4-morpholino-2-butynoic acid in 10 mL of tetrahydrofuran under N2. After stirring for 30 min, a solution of 0.250 g (0.74 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 8 mL of pyridine was added and the mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice water and then poured into saturated sodium bicarbonate and brine. The product was collected, washed with ethyl acetate, and dried in vacuo to give 0.096 g (27%) of yellow solid; ESMS m/z 490.1 (M+H+); mp 112-115° C.

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with ice water
  3. additionpoured into saturated sodium bicarbonate and brine
  4. customThe product was collected
  5. washwashed with ethyl acetate
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1c64df2b6699455a9ffb01df021c6ad2
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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