5-Chloro-2-benzoxazolamine → HCID 57478351, compound

HRID 1179591Notes

Reaction equation

HRID 1179591 reaction equation
C(N(CC)CC)C.Cl[C:9](Cl)([O:11]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][C:39]3[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=3)[NH2:42])[CH2:33][CH2:32]2)[N:22]=1.C(N(C(C)C)CC)(C)C.[Cl:55][C:56]1[CH:57]=[CH:58][C:59]2[O:63][C:62]([NH2:64])=[N:61][C:60]=2[CH:65]=1>ClCCl.C(#N)C>[Cl:55][C:56]1[CH:57]=[CH:58][C:59]2[O:63][C:62]([NH:64][C:9]([NH:42][C:41]3[CH:43]=[CH:44][CH:45]=[C:39]([CH2:38][CH2:37][N:34]4[CH2:33][CH2:32][N:31]([C:27]5[CH:26]=[CH:25][CH:24]=[C:23]6[C:28]=5[CH:29]=[CH:30][C:21]([CH3:20])=[N:22]6)[CH2:36][CH2:35]4)[CH:40]=3)=[O:11])=[N:61][C:60]=2[CH:65]=1

Participants

8

Reactant 5

HCID 61035-Chloro-2-benzoxazolamineHCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Product 1

HCID 57478351HCID 57478351, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (6 eq) and then triphosgene (0.5 eq) were added portionwise to a stirred solution of 3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline (D6) (1 eq) in dichloromethane at 0° C. under an inert atmosphere. The reaction was stirred for 1 h. To the mixture were added acetonitrile, diisopropylethylamine (2 eq) and 5-chloro-1,3-benzoxazol-2-amine (1.1 eq). The reaction was stirred for 16 h. The mixture was extracted with dichloromethane and washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by chromatography on SPE cartridge (Silica), using as eluent a gradient from dichloromethane-MeOH 99:1 to dichloromethane-MeOH 98:2, affording the title compound (yield 47%).

Workup

  1. stirringThe reaction was stirred for 16 h
  2. extractionThe mixture was extracted with dichloromethane
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was purified by chromatography on SPE cartridge (Silica)

Sources & evidence

ORD record
ord-330323b37d154d8d94dd8b638be2755b
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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