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Sodium Hydroxide → Methyl 3-fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate

HRID 1685347
Notes
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Reaction equation

HRID 1685347 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[S:12][C:13]([S:16][C:17]#N)=[CH:14][N:15]=2)=[N:8][CH:9]=1.SC[C@H]([C@@H](CS)O)O.ClC1[CH:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH3:37])=[O:35])[C:29]=1[F:38].[OH-].[Na+]>CO>[F:38][C:29]1[C:30]([C:34]([O:36][CH3:37])=[O:35])=[N:31][CH:32]=[CH:33][C:17]=1[S:16][C:13]1[S:12][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][O:2][CH3:1])=[CH:9][N:8]=2)=[N:15][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 446094D-1,4-DithiothreitolHCID 59200355Methyl 4-chloro-3-fluoropicolinateHCID 59200492N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine

Product 1

HCID 59200467Methyl 3-fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinateYield 39%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A suspension of N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine (0.109 g, 0.392 mmol) in methanol (15 mL) was bubbled with argon for 10 minutes and then treated with dithiothreitol (0.079 g, 0.510 mmol). The reaction was stirred at 23° C. for 10 minutes, then methyl 4-chloro-3-fluoropicolinate (0.0743 g, 0.392 mmol) was added, followed by aq. NaOH (1N, 0.43 mL, 0.431 mmol). The resulting brown solution was stirred for 45 minutes, then concentrated to about one quarter of the volume, diluted in water (15 mL) and neutralized with aq. sat. ammonium chloride. The precipitate was filtered to give the crude title material (0.062 g, 39%) as a solid which was used as such in the next reaction. HPLC ret. time (Condition A): 1.625 min. LC/MS (M+H)+: 407.

Workup

  1. customwas bubbled with argon for 10 minutes
  2. stirringThe resulting brown solution was stirred for 45 minutes
  3. concentrationconcentrated to about one quarter of the volume
  4. additiondiluted in water (15 mL)
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-e8ed54254a3948f1a4c0b8a6ec896a3c
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148400B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes