Hydrochloric Acid → HCID 21074213, compound

HRID 1373188Notes

Reaction equation

HRID 1373188 reaction equation
[OH-].[Na+].[CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[CH:25]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][N:14]=1)=[O:11])([CH3:5])[CH3:4].O.Cl>C1COCC1>[CH:3]([O:6][C:7]1[CH:8]=[C:9]([CH:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[CH:25]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:14]=1)=[O:11])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58780898HCID 58780898, compound

Product 1

HCID 21074213HCID 21074213, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2M NaOH (0.55 ml, 1.1 mM) was added to methyl 2-[3-isopropyloxy-5-(2-fluorophenoxy) methyl benzoyl]amino-5-pyridine carboxylate (0.16 g, 0.36 mM) in THF (10 ml)/water (10 ml) at ambient temperature. After 4 hrs the reaction mixture was neutralised to pH=4–5 with 2M HCl, concentrated, filtered, washed with water, and dried under high-vacuum to give the title compound as a colourless solid (0.15 g, 98%); 1H NMR δ (d6-DMSO): 1.28 (d, 6H), 4.74 (m, 1H), 5.20 (s, 2H), 6.87–6.97 (m, 1H), 7.10 (m, 1H), 7.16–7.26 (m, 3H), 7.54 (s, 1H), 7.66 (s, 1H), 8.28 (s, 2H), 8.84 (s, 1H), 11.78 (bs, 1H).

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. washwashed with water
  4. customdried under high-vacuum

Sources & evidence

ORD record
ord-47308f208017459f8063a76e0a2eac28
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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