Hydrochloric Acid → HCID 59200469, compound

HRID 1685357Notes

Reaction equation

HRID 1685357 reaction equation
[F:1][C:2]1[C:3]([C:24]([O:26]C)=[O:25])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[C:20]3[CH:21]=[CH:22][S:23][C:19]=3[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1.[OH-].[Na+].Cl>O>[F:1][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[C:20]3[CH:21]=[CH:22][S:23][C:19]=3[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59200415HCID 59200415, compound

Product 1

HCID 59200469HCID 59200469, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-fluoro-4-(2-(thieno[3,2-c]pyridin-4-ylamino)thiazol-5-ylthio)picolinate (3.13 g, 7.48 mmol) was treated with aqueous sodium hydroxide (1N, 12 mL, 12.0 mmol) and was stirred at room temperature for 2 hours. The reaction was then acidified to pH ˜6 with 10% aqueous HCl and then poured into water (300 mL) and allowed to sit overnight for complete precipitation. The solid was collected by filtration, washed with water and air dried to give the title material (1.86 g, 62%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.24 (1H, s), 8.22 (1H, d, J=5.56 Hz), 8.18 (1H, d, J=5.05 Hz), 8.15 (1H, d, J=5.81 Hz), 7.90 (1H, s), 7.87 (1H, d, J=5.56 Hz), 7.69 (1H, d, J=5.56 Hz), 6.94 (1H, t, J=5.31 Hz). LC/MS (M+H)+: 405. HPLC ret. time (Condition I): 1.28 min.

Workup

  1. customto sit overnight for complete precipitation
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-43388e777b0a42fd89ed01ac40b3dc59
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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