Hydrochloric Acid → 1-{5-[6-(3-Methylamino-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone diacetate

HRID 870633Notes

Reaction equation

HRID 870633 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]([C:16](=[O:18])[CH3:17])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.C([O:23][C:24](=[O:31])[N:25]([CH2:27][CH2:28][CH2:29][NH2:30])C)(C)(C)C.Cl>CO>[C:16]([OH:18])(=[O:23])[CH3:17].[C:24]([OH:23])(=[O:31])[CH3:2].[CH3:24][NH:25][CH2:27][CH2:28][CH2:29][NH:30][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:15][C:14]([C:16](=[O:18])[CH3:17])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamateHCID 866963171-[5-(6-Fluoro-imidazo[1,2-b]pyridazin-3-yl)-thiophen-2-yl]-ethanone

Product 1

HCID 866963281-{5-[6-(3-Methylamino-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone diacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared as in example 5.6.3 from 1-[5-(6-fluoro-imidazo[1,2-b]pyridazine-3-yl)-thiophen-2-yl]-ethanone (50 mg, 0.2 mmol) and N-(3-aminopropyl)-N-methylcarbamic acid tert-butyl ester [150349-36-3] (72 mg, 0.4 mmol) and deprotected with anhydrous HCl in methanol. Purification by preparative RP-HPLC provided 1-{5-[6-(3-methylamino-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone diacetate as a yellow solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.92-1.96 (m, 5H) 2.24 (t, J=7.45 Hz, 1H) 2.62 (s, 2H) 2.80 (s, 2H) 3.23-3.31 (m, 2H) 3.61 (t, J=7.33 Hz, 1H) 6.79 (d, J=9.60 Hz, 1H) 7.70-7.74 (m, 1H) 7.92 (d, J=4.04 Hz, 1H) 8.06 (br. s., 1H). LRMS (ESI) m/z 330.1 [(M+H)]+, calc'd for C16H19N5OS: 329.43.

Workup

  1. customPurification by preparative RP-HPLC

Sources & evidence

ORD record
ord-39a63dd884eb4b77b2dc64486174858f
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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