Dimethylformamide → HCID 58965023, compound

HRID 913361Notes

Reaction equation

HRID 913361 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[S:18][C:17]([CH2:19][CH2:20][CH3:21])=[N:16][C:10]=3[C:11]([NH2:15])=[N:12][C:13]=2[CH:14]=1)(=O)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.Cl.ClCC1[N:37]=[CH:38][S:39][CH:40]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:19]([C:17]1[S:18][C:9]2[C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:1][C:2]4[N:37]=[CH:38][S:39][CH:40]=4)=[CH:14][C:13]=3[N:12]=[C:11]([NH2:15])[C:10]=2[N:16]=1)[CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride2×HCID 67393211HCID 67393211, compound

Product 1

HCID 58965023HCID 58965023, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-amino-2-propylthiazolo[4,5-c]quinolin-7-ol acetate (318 mg, 1.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), tetrabutylammonium bromide (322 mg, 1.0 mmol), and DMF (15 mL) was stirred at 75° C. for 10 minutes. 4-(Chloromethyl)thiazole hydrochloride (187 mg, 1.1 mmol) was added. Additional 4-(chloromethyl)thiazole hydrochloride (1 eq. total) was added in small portions over a period of 3 hours. The reaction mixture was poured into water (100 mL). A solid was isolated by filtration, allowed to dry, dissolved in dichloromethane, and then purified by HPFC eluting with a gradient of 0-25% CMA in chloroform over 1400 mL and then 25% CMA in chloroform over 600 mL. The resulting solid was recrystallized from acetonitrile to provide 200 mg of 2-propyl-7-[(thiazol-4-yl)methoxy]thiazolo[4,5-c]quinolin-4-amine as an off-white solid, mp 218.0-220.0° C. MS (APCI) m/z 357 (M+H)+; Anal. calcd for C17H16N4OS2.0.2H2O: C, 56.71; H, 4.59; N, 15.56. Found C, 56.66; H, 4.29; N, 15.45.

Workup

  1. customA solid was isolated by filtration
  2. customto dry
  3. dissolutiondissolved in dichloromethane
  4. custompurified by HPFC
  5. washeluting with a gradient of 0-25% CMA in chloroform over 1400 mL
  6. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4c3725b3d52440fd87cc193726f52bb5
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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