Sodium Carbonate → HCID 178525144, compound

HRID 1711406Notes

Reaction equation

HRID 1711406 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([CH2:25][S:26]([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:39]([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.Cl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:19]=[C:20]3[C:21](=[CH:22][CH:23]=2)[NH:24][N:39]=[C:25]3[S:26]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 58828635HCID 58828635, compound

Product 1

HCID 178525144HCID 178525144, compoundYield 55.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 4-[4-amino-3-(1-naphthylsulfonylmethyl)phenoxy]piperidin-1-ylcarboxylic acid benzyl ester (3.2 g, 6.0 mmol) in ethanol and 1.0 N HCl (155 mL) was heated to aid dissolution, treated slowly with sodium nitrite (0.67 g, 9.7 mmol) in water, stirred at ambient temperatures for one hour, basified with solid sodium carbonate, stirred at ambient temperature for 1 hour and concentrated in vacuo. The resultant residue was partitioned in ethyl acetate and brine. The phases were separated; the organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. This residue was purified by flash chromatography with 35-40% ethyl acetate in hexane and 100% ethyl acetate to give 4-[3-(1-naphthylsulfonyl)-1H-indazol-5-yloxy]piperidin-1-ylcarboxylic acid benzyl ester as a light orange foam, 1.79 g (55.9% yield), Mass spectrum (+EI, [M+H]+) m/z 542. 1HNMR (500 MHz, DMSO-d6): δ14.07 (s, 1H), 8.71-8.73 (m, 1H), 8.55 (dd, 1H, J=7.45 Hz and 1.22 Hz), 8.26 (d, 1H, J=8.29 Hz), 8.01-8.03 (m, 1H), 7.70-7.74 (m, 1H), 7.51-7.62 (m, 3H), 7.27-7.35 (m, 5H), 7.23 (d, 1H, J=2.20 Hz), 7.09 (dd, 1H, J=9.03 Hz and 2.32 Hz), 5.06 (s, 2H), 4.59-4.61 (m, 1H), 3.63-3.72 (m, 2H), 3.29-3.33 (m, 2H), 1.83-1.88 (m, 2H), 1.50-1.55 ppm (m, 2H

Workup

  1. temperaturewas heated
  2. dissolutiondissolution
  3. stirringstirred at ambient temperature for 1 hour
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was partitioned in ethyl acetate
  6. customThe phases were separated
  7. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThis residue was purified by flash chromatography with 35-40% ethyl acetate in hexane and 100% ethyl acetate

Sources & evidence

ORD record
ord-2b445f7a2b114114b9d2cb1fd363a948
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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