2-Methylbutylamine → 1-{5-[6-(2-Methyl-butylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone

HRID 870635Notes

Reaction equation

HRID 870635 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.[CH3:19][CH:20]([CH2:23][CH3:24])[CH2:21][NH2:22]>>[CH3:19][CH:20]([CH2:23][CH3:24])[CH2:21][NH:22][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

3

Reactant 2

HCID 72832-MethylbutylamineHCID 866963171-[5-(6-Fluoro-imidazo[1,2-b]pyridazin-3-yl)-thiophen-2-yl]-ethanone

Product 1

HCID 898024131-{5-[6-(2-Methyl-butylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone

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 racemic 2-methylbutylamine [96-15-1] (42 mg, 0.5 mmol). Purification by preparative RP-HPLC provided 1-{5-[6-(2-methyl-butylamino)-imidazo[1,2-b]pyridazin-3-yl]-thiophen-2-yl}-ethanone as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.88-1.01 (m, 5H) 1.19-1.30 (m, 1H) 1.50-1.61 (m, 4H) 1.89 (dq, J=13.29, 6.74 Hz, 1H) 2.54 (s, 2H) 3.26-3.33 (m, 1H) 3.40-3.49 (m, 1H) 4.57 (t, J=5.73 Hz, 1H) 6.43-6.47 (m, 1H) 7.21 (s, 1H) 7.56-7.58 (m, 1H) 7.61-7.67 (m, 2H) 7.90 (s, 1H). LRMS (ESI) m/z 329.1 [(M+H)]+, calc'd for C17H20N40S: 328.44.

Workup

  1. customPurification by preparative RP-HPLC

Sources & evidence

ORD record
ord-afcf9af269304725a46e72e695e0daad
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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