Triethylamine → Tert-butyl 4-{4-[5-(5-tert-butyl-3-methanesulphinyl-2-methoxy-phenylcarbamoyl)-2-methyl-phenoxy]-pyridin-2-ylmethyl}-piperidine-1-carboxylate

HRID 1844609Notes

Reaction equation

HRID 1844609 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:31])=[C:8]([CH:30]=1)[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[CH:11]=1)(O)=[O:2].[C:32]([C:36]1[CH:37]=[C:38]([S:45]([CH3:47])=[O:46])[C:39]([O:43][CH3:44])=[C:40]([CH:42]=1)[NH2:41])([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>C(OCC)(=O)C.O1CCCC1>[C:32]([C:36]1[CH:37]=[C:38]([S:45]([CH3:47])=[O:46])[C:39]([O:43][CH3:44])=[C:40]([NH:41][C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:31])=[C:8]([CH:30]=2)[O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:21][CH2:22]3)[CH:11]=2)=[O:2])[CH:42]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 584939605-Tert-butyl-3-methanesulphinyl-2-methoxy-phenylamineHCID 67491557Tert-butyl 4-[4-(5-carboxy-2-methyl-phenoxy)-pyridin-2-ylmethyl]-piperidine-1-carboxylate

Product 1

HCID 67491299Tert-butyl 4-{4-[5-(5-tert-butyl-3-methanesulphinyl-2-methoxy-phenylcarbamoyl)-2-methyl-phenoxy]-pyridin-2-ylmethyl}-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

At ambient temperature 560 μl of a 50% solution of propanephosphoric acid cycloanhydride in ethyl acetate are added to a solution of 120 mg tert-butyl 4-[4-(5-carboxy-2-methyl-phenoxy)-pyridin-2-ylmethyl]-piperidine-1-carboxylate, 68 mg 5-tert-butyl-3-methanesulphinyl-2-methoxy-aniline and 145 μl triethylamine in 4 ml of tetrahydrofuran. The solution is heated to 80° C. and stirred overnight at this temperature. Then the solution is evaporated to dryness and the residue is combined with saturated aqueous NaHCO3 solution and ethyl acetate. The organic phase is separated off and washed with water and saturated aqueous saline solution and dried (Na2SO4). The solvent is evaporated off, and the residue is chromatographed on silica gel with dichloromethane/10% methanolic ammonia solution (99:1→90:10) as eluant.

Workup

  1. customThen the solution is evaporated to dryness
  2. customThe organic phase is separated off
  3. washwashed with water and saturated aqueous saline solution
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is evaporated off
  6. customthe residue is chromatographed on silica gel with dichloromethane/10% methanolic ammonia solution (99:1→90:10) as eluant

Sources & evidence

ORD record
ord-2e7aa35e3e764041b6aeb32035211677
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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