4-bromo-5-methoxy-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline → 5-chloro-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine

HRID 1848024Notes

Reaction equation

HRID 1848024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[C:5]([NH:8][CH2:9][C:10]2[CH:20]=[CH:19][C:13]3[N:14]=[C:15]([S:17][CH3:18])[S:16][C:12]=3[CH:11]=2)=[N:6][CH:7]=1.BrC1C(OC)=CC(NCC2C=CC3N=C(SC)SC=3C=2)=C([N+]([O-])=O)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]([NH:8][CH2:9][C:10]2[CH:20]=[CH:19][C:13]3[N:14]=[C:15]([S:17][CH3:18])[S:16][C:12]=3[CH:11]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 866810294-bromo-5-methoxy-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroanilineHCID 866810425-Chloro-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine

Product 1

HCID 866810415-chloro-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamineYield 65%

Procedure

Crude 5-chloro-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine was synthesized as a yellow solid using a procedure analogous to that describe in Step 2 of Example 41, substituting 5-chloro-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine from Step 1 of this Example for 4-bromo-5-methoxy-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline used in Example 41. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc to afford 5-chloro-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine (75 mg, 65%). LCMS (ESI) m/z 337 (M+H)+.

Workup

  1. customCrude 5-chloro-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine was synthesized as a yellow solid
  2. customThe residue was purified by silica gel flash chromatography
  3. washeluting with a gradient of 100% hexanes to 100% EtOAc

Sources & evidence

ORD record
ord-01b70b52b50b4d8da98d859d967dce89
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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