Water → HCID 67393114, compound

HRID 913370Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:15][CH3:16])[S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:17])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][CH2:26][CH2:27][Cl:28].O>CN(C=O)C>[Cl:28][CH2:27][CH2:26][CH2:25][O:17][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[S:14][C:13]([CH2:15][CH3:16])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (1.00 mg, 4.08 mmol), cesium carbonate (5.30 g, 16.3 mmol), and DMF (40 mL) was stirred at 50° C. for 10 minutes. A portion (0.05 mL) of a solution (1.1 mL) of 1-bromo-3-chloropropane (705 mg, 4.48 mmol) in DMF was added every 7 minutes. After 2 hours the reaction mixture was poured into water (225 mL). The mixture was stirred for 30 minutes and then filtered. The isolated solid was dried to provide 785 mg of 7-(3-chloropropoxy)-2-ethylthiazolo[4,5-c]quinolin-4-amine as a brown solid.

Workup

stirringThe mixture was stirred for 30 minutes
filtrationfiltered
customThe isolated solid was dried

Sources & evidence

ORD record: ord-5b520ac176224a42ab9cf020e9d3a5ce
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026366B2

Reaction notes

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