Sodium Bicarbonate → HCID 67453311, compound

HRID 2090820Notes

Reaction equation

HRID 2090820 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C@H:22]([CH2:23][O:24][CH2:25][C:26](O)=[O:27])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1.[CH3:30][N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:33][CH2:32]1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C@H:22]([CH2:23][O:24][CH2:25][C:26]([N:41]3[CH2:40][CH2:39][N:38]([CH2:37][CH:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)[CH2:43][CH2:42]3)=[O:27])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 59820104HCID 59820104, compound

Product 1

HCID 67453311HCID 67453311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N′-Carbonyldiimidazole (131 mg, 0.813 mmol) was added to a solution of (S)-2-((2-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)methoxy)-acetic acid (step d, Example 127) (325 mg, 0.775 mmol) in dichloromethane (5 ml), and stirring was carried out for 2 h at 30° C. A solution of 1-((1-methylpiperidin-4-yl)methyl)piperazine (152 mg, 0.775 mmol) in dichloromethane (5 ml) was then added at room temperature, and the reaction mixture was stirred for 15 h at that temperature. Saturated sodium hydrogen carbonate solution (10 ml) was added to the mixture, and the aqueous phase was extracted with dichloromethane (20 ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) using ethyl acetate/methanol/ammonia solution (25% aq.) (40:10:0.5). Yield: 263 mg (57%); MS, m/z 599.3 (MW).

Workup

  1. stirringthe reaction mixture was stirred for 15 h at that temperature
  2. extractionthe aqueous phase was extracted with dichloromethane (20 ml)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-b4bf912150ae454b984b817f15649c82
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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