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

HRID 1685347Notes

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

Participants

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

customwas bubbled with argon for 10 minutes
stirringThe resulting brown solution was stirred for 45 minutes
concentrationconcentrated to about one quarter of the volume
additiondiluted in water (15 mL)
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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