Methanol → HCID 178424414, compound

HRID 909260Notes

Reaction equation

HRID 909260 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])(=[O:21])=[O:20])[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:29](C=P(CCCC)(CCCC)CCCC)#N.CO>C1(C)C=CC=CC=1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]([CH3:29])[S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])(=[O:21])=[O:20])[CH2:14][CH2:13]2)=[O:11])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 178424415HCID 178424415, compound

Product 1

HCID 178424414HCID 178424414, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 41 mg (0.1 mmol) N-{trans-4-[(4-isopropylpiperazin-1-yl)carbonyl]cyclohexyl}-2-methylbenzenesulfonamide (example 4), 72 mg (0.3 mmol) cyanomethylene tri-n-butylphosphorane and 32 mg (1 mmol) methanol in 2 mL toluene was heated for 16 h to 110° C. After evaporation methanol and DMF were added and the mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.1% NEt3). The combined product fractions were evaporated to dryness to yield 12.4 mg (29%) of the title compound. MS (m/e): 422.2 (MH+).

Workup

  1. temperaturewas heated for 16 h to 110° C
  2. customAfter evaporation methanol and DMF
  3. additionwere added
  4. customthe mixture was subjected to preparative HPLC purification on reversed phase
  5. washeluting with a gradient of acetonitrile/water (0.1% NEt3)
  6. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-c2c5eff67ae941fb9797ccca0317d574
Source dataset
uspto-grants-2011_09
Patent number
US08017773B2

Reaction notes

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