Ammonium Chloride → HCID 57898983, compound

HRID 911019Notes

Reaction equation

HRID 911019 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[C:19]([S:20][CH2:21][CH2:22][C:23](OC)=O)=[CH:18][N:17]=[C:16]([NH:27][C:28]2[S:29][CH:30]=[C:31]([CH3:33])[N:32]=2)[CH:15]=1.CC([O-])(C)C.[K+].Br.BrC[C:43]1[CH:48]=[CH:47]C=C[N:44]=1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][C:14]1[C:19]([S:20][CH2:21][C:22]2[CH:23]=[CH:47][CH:48]=[CH:43][N:44]=2)=[CH:18][N:17]=[C:16]([NH:27][C:28]2[S:29][CH:30]=[C:31]([CH3:33])[N:32]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 23665647Potassium tert-butoxideHCID 86634749HCID 86634749, compound

Product 1

HCID 57898983HCID 57898983, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 20 mL vial is charged with ethyl 4-chloro-3-(5-(3-methoxy-3-oxopropylthio)-2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (0.33 mmol) and THF (0.5 mL). 1M KOtBu in THF (1.184 ml, 1.184 mmol) is added and the reaction mixture is stirred at room temperature for 30 seconds. 2-(Bromomethyl)pyridine hydrobromide (85.55 mg, 0.3382 mmol) is added and the reaction mixture is stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride is added and extracted with EtOAc. The reaction mixture is purified via column chromatography on silica gel to afford ethyl 4-chloro-3-(2-(4-methylthiazol-2-ylamino)-5-(pyridin-2-ylmethylthio)pyridin-4-yloxy)benzoate.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc
  3. customThe reaction mixture is purified via column chromatography on silica gel

Sources & evidence

ORD record
ord-5b3bd566412b4816b129c82a60de3c6c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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