Dimethylformamide → HCID 58965032, compound

HRID 913363Notes

Reaction equation

HRID 913363 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.BrCC[N:36]1[CH:40]=[CH:39][CH:38]=[CH:37]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][CH2:2][N:36]4[CH:40]=[CH:39][CH:38]=[CH:37]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 carbonate3×HCID 116512251-(2-Bromoethyl)pyrrole3×HCID 67393211HCID 67393211, compound

Product 1

HCID 58965032HCID 58965032, compoundYield 40.6%

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. 1-(2-Bromoethyl)pyrrole (200 mg, 1.1 mmol) was added dropwise over a period of 10 minutes. After 3 hours an additional equivalent of cesium carbonate was added in a single portion followed by the dropwise addition of an equivalent of 1-(2-bromoethyl)pyrrole. The reaction mixture was stirred overnight and then an additional equivalent of both cesium carbonate and 1-(2-bromoethyl)pyrrole were added. After 1 hour the heat source was removed; 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 0-15% CMA in chloroform over 1500 mL. The resulting solid was recrystallized from acetonitrile to provide 143 mg of 2-propyl-7-[2-(pyrrol-1-yl)ethoxy]thiazolo[4,5-c]quinolin-4-amine as an off-white solid, mp 158.0-160.0° C. MS (ESI) m/z 353 (M+H)+; Anal. calcd for C19H20N4OS: C, 64.75; H, 5.72; N, 15.90. Found C, 64.86; H, 5.38; N, 16.00.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customAfter 1 hour the heat source was removed
  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 0-15% CMA in chloroform over 1500 mL
  11. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8bbf73b9472c4fabbc1be31a80a42f2d
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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