Diisopropylethylamine → HCID 86690491, compound

HRID 1026765Notes

Reaction equation

HRID 1026765 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][NH:16][CH:17]3[CH2:20][CH2:19][CH2:18]3)[N:14]=2)=[CH:6][CH:5]=1.[CH3:23][N:24]1[CH:28]=[C:27]([C:29](O)=[O:30])[N:26]=[CH:25]1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(#N)C.O>[CH:17]1([N:16]([CH2:15][C:13]2[N:14]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=3)[S:11][CH:12]=2)[C:29]([C:27]2[N:26]=[CH:25][N:24]([CH3:23])[CH:28]=2)=[O:30])[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate MethanaminiumHCID 86690492HCID 86690492, compound

Product 1

HCID 86690491HCID 86690491, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of N-({2-[4-(trifluoromethoxy)phenyl]-1,3-thiazol-4-yl}methyl)cyclobutaneamine (430 mg), methyl-1H-imidazole-4-carboxylic acid (451 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (598 mg) and diisopropylethylamine (0.69 mL) in acetonitrile (15 mL) was stirred at room temperature for 3 days. Water was added to the reaction mixture, followed by extraction with chloroform. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) and PTLC (silica gel, chloroform:methanol=19:1). The resulting residue was re-crystalized with isopropyl ether to afford the title compound (216 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) and PTLC (silica gel, chloroform:methanol=19:1)
  4. customThe resulting residue was re-crystalized with isopropyl ether

Sources & evidence

ORD record
ord-051d8fb2d124445d9829717e6b69daa1
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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