2-(2-Tert-butylphenoxy)pyridin-3-amine → HCID 59857463, compound

HRID 2377818Notes

Reaction equation

HRID 2377818 reaction equation
N=[S:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[C:13]([C:17]1[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=1[O:19][C:20]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][N:21]=1)([CH3:16])([CH3:15])[CH3:14]>CO>[C:13]([C:17]1[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=1[O:19][C:20]1[C:25]([NH:26][C:3]2[S:2][C:6]3[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=3[N:4]=2)=[CH:24][CH:23]=[CH:22][N:21]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 286054272-(2-Tert-butylphenoxy)pyridin-3-amineHCID 66987529HCID 66987529, compound

Product 1

HCID 59857463HCID 59857463, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.38 mmol) of 1-imino-6-methoxybenzothiazole and 1b were heated under N2 atmosphere at 220° C. for 30 min, in a similar manner to 234a. After cooling to rt, the reaction mixture was suspended in MeOH and the side product bis(6-methoxybenzo[d]thiazol-2-yl)amine (46.3 mg) was eliminated by filtration. The mother liquors were purified by preparative HPLC to yield Example 233. tR=7.861 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna 4.6×50 mm; flow rate 2.5 mL/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4 & B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C23H24N3O2S [M+H]+406.1589, found 406.1576.

Workup

  1. filtrationthe side product bis(6-methoxybenzo[d]thiazol-2-yl)amine (46.3 mg) was eliminated by filtration
  2. customThe mother liquors were purified by preparative HPLC
  3. customto yield Example 233
  4. washGradient elution 0% to 100% B over 8 min

Sources & evidence

ORD record
ord-b8684c7e03db4b8a97401ef3fec6ec48
Source dataset
uspto-grants-2008_12
Patent number
US07470712B2

Reaction notes

Loading…