Dimethylformamide → HCID 58965028, compound

HRID 913362Notes

Reaction equation

HRID 913362 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.I.I[CH2:35][C:36]1[CH:37]=[N:38][CH:39]=CC=1>ClCCl>[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[CH:39]=[N:38][CH:37]=[CH:36][CH:35]=4)=[CH:14][C:13]=3[N:12]=[C:11]([NH2:15])[C:10]=2[N:16]=1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 162131823-(Iodomethyl)pyridine--hydrogen iodide (1/1)HCID 67393211HCID 67393211, compound

Product 1

HCID 58965028HCID 58965028, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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), and DMF (20 mL) was stirred at 75° C. for 10 minutes. 3-(Iodomethyl)pyridine hydroiodide (381 mg, 1.1 mmol) was added in portions over a period of 3 hours. The heat source was removed and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (250 mL), stirred for 1 hour, and then filtered. The isolated solid was rinsed with water and then dried to provide a brown powder. This material was dissolved in dichloromethane and then purified by HPFC eluting with a gradient of 0-20% CMA in chloroform over 1400 mL and then 20% CMA in chloroform over 600 mL. The resulting solid was recrystallized from acetonitrile to provide 160 mg of 2-propyl-7-[(pyridin-3-yl)methoxy]thiazolo[4,5-c]quinolin-4-amine as an off-white solid, mp 167.0-169.0° C. MS (APCI) m/z 351 (M+H)+; Anal. calcd for C19H18N4OS: C, 65.12; H, 5.18; N, 15.99. Found C, 65.25; H, 5.06; N, 16.03.

Workup

  1. customThe heat source was removed
  2. stirringthe reaction mixture was stirred at ambient temperature overnight
  3. additionThe reaction mixture was diluted with water (250 mL)
  4. stirringstirred for 1 hour
  5. filtrationfiltered
  6. washThe isolated solid was rinsed with water
  7. customdried
  8. customto provide a brown powder
  9. custompurified by HPFC
  10. washeluting with a gradient of 0-20% CMA in chloroform over 1400 mL
  11. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5e26963a11c140c3affb89fa67ea67f4
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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