Sodium Methoxide → 6-Chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid sodium salt

HRID 1626528Notes

Reaction equation

HRID 1626528 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:36])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([CH:33]4[CH2:35][CH2:34]4)=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:37]([OH:39])=[O:38].C[O-].[Na+:42]>CO>[Na+:42].[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:36])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([CH:33]4[CH2:34][CH2:35]4)=[N:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][CH:28]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:37]([O-:39])=[O:38]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 672876146-Chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid

Product 1

HCID 672876286-Chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid sodium saltYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-Chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (15 mg, 0.027 mmol) was diluted with methanol (1 mL) followed by the addition of NaOMe in methanol (53 μL, 0.027 mmol). After stirring for 2 hours, the reaction was concentrated and dried under high vacuum pressure for 2 hours. The material was diluted with hexanes, sonicated and concentrated to afford 6-chloro-7-(4-(2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid sodium salt (15 mg, 0.027 mmol, 100% yield) as a white solid. MS (es+apci, positive) m/z=561.1. 1H NMR (400 MHz, D6 DMSO) δ 8.59 (br s, 1H), 7.81 (d, 2H), 7.75 (d, 1H), 7.54 (d, 1H), 7.49 (s, 1H), 6.95 (d, 2H), 6.57 (s, 1H), 4.17 (br s, 2H), 3.55-3.53 (m, 3H), 3.35-3.31 (m, 4H), 3.11-3.09 (m, 2H), 2.47-2.43 (m, 1H), 2.21-2.17 (m, 1H), 1.92-1.87 (m, 1H).

Workup

  1. concentrationthe reaction was concentrated
  2. customdried under high vacuum pressure for 2 hours
  3. additionThe material was diluted with hexanes
  4. customsonicated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb78b447dae34016870870d65a59c946
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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