4-Methylmorpholine → 4-(1,1-Dimethylethyl)-N-[5-[[[3-[[4-(2-pyrimidinyl)piperazin-1-yl]carbonyl]-4-methylphenyl]thio]methyl]thiazol-2-yl]benzamide

HRID 49145

Reaction equation

HRID 49145 reaction equation
[CH3:1][C:2]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[S:13][C:14]([CH2:17][S:18][C:19]3[CH:20]=[CH:21][C:22]([CH3:28])=[C:23]([CH:27]=3)[C:24](O)=[O:25])=[CH:15][N:16]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[N:31]1[CH:36]=[CH:35][CH:34]=[N:33][C:32]=1[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[S:13][C:14]([CH2:17][S:18][C:19]3[CH:20]=[CH:21][C:22]([CH3:28])=[C:23]([C:24]([N:40]4[CH2:41][CH2:42][N:37]([C:32]5[N:31]=[CH:36][CH:35]=[CH:34][N:33]=5)[CH2:38][CH2:39]4)=[O:25])[CH:27]=3)=[CH:15][N:16]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 887471-(2-Pyrimidinyl)piperazineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 221704385-[[[2-[[4-(1,1-Dimethylethyl)benzoyl]amino]thiazol-5-yl]methyl]thio]-2-methylbenzoic acid

Product 1

HCID 221704044-(1,1-Dimethylethyl)-N-[5-[[[3-[[4-(2-pyrimidinyl)piperazin-1-yl]carbonyl]-4-methylphenyl]thio]methyl]thiazol-2-yl]benzamideYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of the product of Example 32, part B (0.250 g, 0.567 mmol), 1-(2-pyrimidyl) piperazine (0.121 g, 0.737 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphoniumhexafluorophosphate (0.476 g, 1.08 mmol), 4-methylmorpholine (0.31 mL, 2.82 mmol) in DMF (6 mL) was heated at 65° C. for 5 h. The mixture was then diluted with ethyl acetate, washed with water, 1N NaOH solution, water, and brine. The solution was dried over anhydrous MgSO4 and concentrated under vacuum. The residue was purified using flash column chromatography (ethyl acetate) to provide the desired product (0.210 g, 63%) as a white solid: LC/MS RT=3.94 min; mass spectrum (M+H)+=587.42.

Workup

  1. washwashed with water, 1N NaOH solution, water, and brine
  2. dry with materialThe solution was dried over anhydrous MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified

Sources & evidence

ORD record
ord-6a2c7fc5157c40d3b014389aa8186262
Source dataset
uspto-grants-2004_03
Patent number
US06706717B2

Linked notes

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