Pyridine → N-cyclohexyl-N-methyl-4-(2-oxo-3-methylene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide

HRID 651999Notes

Reaction equation

HRID 651999 reaction equation
N1C=CC=CC=1.[CH:7]1([N:13]([CH3:36])[C:14](=[O:35])[CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]2[NH:29][C:30](=[O:34])[CH:31]([CH2:32]O)[N:23]2[CH2:22]3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.S(Cl)(C)(=O)=O.CCN(C(C)C)C(C)C>O>[CH:7]1([N:13]([CH3:36])[C:14](=[O:35])[CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]2[NH:29][C:30](=[O:34])[C:31](=[CH2:32])[N:23]2[CH2:22]3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 135626245N-cyclohexyl-N-methyl-4-(2-oxo-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide

Product 1

HCID 135626217N-cyclohexyl-N-methyl-4-(2-oxo-3-methylene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 500 ml of pyridine was added 5.14 g of N-cyclohexyl-N-methyl-4-(2-oxo-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide to which was added 0.9 ml of mesyl chloride. This solution was cooled to about 0°-5° C., at which time 7.12 ml of DIPEA was added. This solution was stirred at room temperature for 3 hours. The pyridine was stripped under high vacuum at about 40° C. to give a suspension which was trituratured with water, centrifuged and crystals of the captioned compound collected by filtration: m.p. 176°-178° C.

Workup

  1. additionwas added
  2. customwas stripped under high vacuum at about 40° C.
  3. customto give a suspension which
  4. filtrationcentrifuged and crystals of the captioned compound collected by filtration

Sources & evidence

ORD record
ord-64ab45fecbd14e4f907222146ad656fa
Source dataset
uspto-grants-1987_06
Patent number
US04670434

Reaction notes

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