Ethanol → HCID 67287710, compound

HRID 1626517Notes

Reaction equation

HRID 1626517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:32][CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([O:37]CC)=[O:36].[OH-].[Na+].C(O)C>O1CCCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:34])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:32][CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67287388HCID 67287388, compound

Product 1

HCID 67287710HCID 67287710, compoundYield 55.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylate (133 mg, 0.241 mmol) was diluted with tetrahydrofuran (2 mL) followed by the addition of aqueous NaOH (603 μL, 1.21 mmol) and ethanol (1 mL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 2N aqueous HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (70 mg, 0.134 mmol, 55.5% yield). MS (es+apci, positive) m/z=523.2. 1H NMR (400 MHz, CDCl3) δ 7.71 (d, 2H), 7.42 (s, 1H), 7.35 (d, 1H), 6.96 (d, 2H), 6.54 (s, 1H), 6.47 (d, 1H), 4.25 (dd, 2H), 3.74 (t, 1H), 3.68 (t, 2H), 3.02 (t, 2H), 2.38-2.32 (m, 1H), 2.19-2.08 (m, 2H), 1.13-1.09 (m, 2H), 0.93-0.89 (m, 2H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-96810233a5b54cb7863086034ea51601
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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