Methylamine → (2-[1-(6-Chloroimidazo[2,1-b]thiazole-5-sulfonyl)-1H-indol-3-yl]ethyl}methyl amine

HRID 1835114Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[N:23]3[C:19]([S:20][CH:21]=[CH:22]3)=[N:18][C:17]=2[Cl:24])(=[O:15])=[O:14])[CH:5]=1.[CH3:25][NH2:26]>C1COCC1>[Cl:24][C:17]1[N:18]=[C:19]2[N:23]([C:16]=1[S:13]([N:6]1[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH2:3][CH2:2][NH:26][CH3:25])=[CH:5]1)(=[O:14])=[O:15])[CH:22]=[CH:21][S:20]2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-(2-bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl)indole (92 mg, 0.20 mmol) in THF is treated with methyl amine (2M in methanol, 0.4 mL, 2 eq.), heated at 50° C. for 24 h, cooled and concentrated in vacuo. The resultant residue is purified by HPLC1 to give the title product as a white solid, 18.5 mg, identified by HPLC2 and mass spectral analyses.

Workup

temperaturecooled
concentrationconcentrated in vacuo
customThe resultant residue is purified by HPLC1

Sources & evidence

ORD record: ord-bc43e3a0f6f749ca96f5060add5a30a2
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770642B2

Reaction notes

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