Triethylamine → HCID 86592782, compound

HRID 1827523Notes

Reaction equation

HRID 1827523 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:41]1([C:47](Cl)=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:41]1([C:47]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=2)[C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:10][CH:11]=2)=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 22137300Toluene-4-sulfonic acid 4-{[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-methyl}-phenyl ester

Product 1

HCID 86592782HCID 86592782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of toluene-4-sulfonic acid 4-{[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-methyl}-phenyl ester (0.120 g, 0.26 mmol) and triethylamine (0.18 mL, 1.36 mmol) in 2 mL methylene chloride was added cyclohexanecarbonyl chloride (0.138 mL, 1.03 mmol). The reaction mixture was stirred for 3 hr. at room temperature. Saturated aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was washed with an additional 2 mL of methylene chloride. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated. Flash filter chromatography afforded the title compound of Step A. MS 577.1 (M+1)+

Workup

  1. customat room temperature
  2. customthe layers were separated
  3. washThe aqueous layer was washed with an additional 2 mL of methylene chloride
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationFlash filter chromatography

Sources & evidence

ORD record
ord-443a858c4b2149d2886baf470a0ffaff
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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