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4-Methylmorpholine → HCID 10164583, compound

HRID 1068984
Notes
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Reaction equation

HRID 1068984 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[CH3:16][O:17][CH2:18][CH2:19][N:20]([CH2:27][CH2:28][O:29][CH3:30])[CH2:21][C:22]#[C:23][C:24]([OH:26])=O.[Br:31][C:32]1[CH:33]=[C:34]([NH:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[C:46]([NH2:49])[CH:47]=3)[N:42]=[CH:41][N:40]=2)[CH:35]=[CH:36][CH:37]=1>O1CCCC1.N1C=CC=CC=1>[Br:31][C:32]1[CH:33]=[C:34]([NH:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[C:46]([NH:49][C:24](=[O:26])[C:23]#[C:22][CH2:21][N:20]([CH2:19][CH2:18][O:17][CH3:16])[CH2:27][CH2:28][O:29][CH3:30])[CH:47]=3)[N:42]=[CH:41][N:40]=2)[CH:35]=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 18548945HCID 18548945, compound

Product 1

HCID 10164583HCID 10164583, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyl chloroformate (0.845 g, 6.2 mmol) and N-methylmorpholine (0.963 g, 9.52 mmol) were added to an ice cold solution of 2.100 g (9.52 mmol) of 4-[bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid in 50 mL of tetrahydrofuran under nitrogen. After stirring for 30 min, a solution of 1.500 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 10 mL of pyridine was added and the mixture was stirred for 2 hr at 0° C. 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 0.660 g of 4-[Bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide: mass spectrum (m/e): M+H 512.

Workup

  1. stirringthe mixture was stirred for 2 hr at 0° C
  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-12cb9f05de374efaa62a6b5d8f3e8661
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06251912B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes