4-Methylmorpholine → HCID 5328985, compound

HRID 1069010Notes

Reaction equation

HRID 1069010 reaction equation
[N:1]1([CH2:7][C:8](=[CH2:12])[C:9]([OH:11])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(OC(Cl)=O)C(C)C.CN1CCOCC1.[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.C(OCC)(=O)C>[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:9](=[O:11])[C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[CH2:12])[CH:44]=3)[N:39]=[CH:38][N:37]=2)[CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 103972322-(Morpholinomethyl)acrylic acid

Product 1

HCID 5328985HCID 5328985, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran solution of 2.06 g (0.012 moles) of 2-Morpholin-4-ylmethyl-acrylic acid in 25 mL of tetrahydrofuran was cooled in an ice bath, and 1.56 mL (1.64 g; 0.012 mole) of isobutylchloroformate was added, giving a precipitate. This was followed by 1.32 mL (1.22 g; 0.012 mole) of N-methylmorpholine. After 2 minutes, 3.15 g (0.01 mole) of N-(3-bromophenyl)-4,6-quinazolindiamine in 25 mL of pyridine was added. Cooling and stirring were continued for 1 ½ hours. Then the reaction was poured onto ice and 25 mL of ethyl acetate. The resulting mixture was extracted with 3 portions of ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over sodium sulfate, and taken to an oil in vacuo. This was washed with water and chromatographed on silica gel. The column was eluted with a gradient ranging from 1:1 ethyl acetate hexanes to 1:19 methanol ethyl acetate. The fifth fraction contained 0.733 g (15%) of the desired product Mass Spectrum (m/e) M+H 235.5.

Workup

  1. customgiving a precipitate
  2. temperatureCooling
  3. customwere continued for 1 ½ hours
  4. extractionThe resulting mixture was extracted with 3 portions of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. washThis was washed with water
  8. customchromatographed on silica gel
  9. washThe column was eluted with a gradient

Sources & evidence

ORD record
ord-dab8c8a4519f47a997dd0e8519e5675e
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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