4-Methylmorpholine → HCID 5328961, compound

HRID 1068975Notes

Reaction equation

HRID 1068975 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[N:16]1([CH2:22][C:23]#[C:24][C:25]([OH:27])=O)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[Br:28][C:29]1[CH:30]=[C:31]([NH:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[C:43]([NH2:46])[CH:44]=3)[N:39]=[CH:38][N:37]=2)[CH:32]=[CH:33][CH:34]=1>O1CCCC1.N1C=CC=CC=1>[Br:28][C:29]1[CH:30]=[C:31]([NH:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[C:43]([NH:46][C:25](=[O:27])[C:24]#[C:23][CH2:22][N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[CH:44]=3)[N:39]=[CH:38][N:37]=2)[CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5419084-Morpholinotetrolic acidHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 5328961HCID 5328961, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (0.343 g, 2.5 mmol) and N-methylmorpholine (0.322 g, 3.18 mmol) were added to an ice cold solution of 0.540 g (3.18 mmol) of 4-morpholin-4-yl-but-2-ynoic acid in 50 mL of tetrahydrofuran under nitrogen. After stirring for 30 min, a solution of 0.500 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 10 mL of pyridine was added and the mixture was stirred at 0° C. for 2 hr. The reaction was then quenched with ice water, poured into saturated sodium bicarbonate, and the product was extracted with ethyl acetate. Chromatography of the extract on silica gel, eluting with methanol/ethyl acetate (15:85), gave 0.240 g of 4-morpholin-4-yl-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide: mass spectrum (m/e): M+H 466.

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 hr
  2. customThe reaction was then quenched with ice water
  3. additionpoured into saturated sodium bicarbonate
  4. extractionthe product was extracted with ethyl acetate
  5. extractionChromatography of the extract on silica gel
  6. washeluting with methanol/ethyl acetate (15:85)

Sources & evidence

ORD record
ord-fb5d98dba48b4b40a0aa44eb20fba78e
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

Loading…