4-Methylmorpholine → HCID 131722712, compound

HRID 1068995Notes

Reaction equation

HRID 1068995 reaction equation
ClC(OC[CH:6]([CH3:8])[CH3:7])=O.CN1CCOCC1.C([C:19]([CH:26](C)C)([NH2:25])[C:20]#[C:21][C:22]([OH:24])=O)(C)C.[Br:29][C:30]1[CH:31]=[C:32]([NH:36][C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[C:44]([NH2:47])[CH:45]=3)[N:40]=[CH:39][N:38]=2)[CH:33]=[CH:34][CH:35]=1.O1C[CH2:51][CH2:50][CH2:49]1>N1C=CC=CC=1>[Br:29][C:30]1[CH:31]=[C:32]([NH:36][C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[C:44]([NH:47][C:22](=[O:24])[C:21]#[C:20][CH:19]([CH3:26])[N:25]([CH:50]([CH3:51])[CH3:49])[CH:6]([CH3:8])[CH3:7])[CH:45]=3)[N:40]=[CH:39][N:38]=2)[CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 21190749HCID 21190749, compound

Product 1

HCID 131722712HCID 131722712, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isobutyl chloroformate (0.845 g, 6.2 mmol) and N-methylmorpholine (1.0 g, 9.9 mmol) were added to an ice cold solution of 1.8 g (9.67 mmol) of diisopropyl-amino-but-2-ynoic acid in 100 mL of tetrahydrofuran under nitrogen. After stirring for 30 min, a solution of 1.500 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 15 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 (5:95), gave 1.54 g of diisopropyl-methyl-amino-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide: mass spectrum (m/e): M+H 480.

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 (5:95)

Sources & evidence

ORD record
ord-627ca5b6a25045adbbad27fda2167f48
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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