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 1294754

Reaction equation

HRID 1294754 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-49abdf0a9b344aa994ddcf49e87f0e67
Source dataset
uspto-grants-2007_07
Patent number
US07241781B2

Linked notes

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