HCID 68481210, compound → HCID 178486271, compound

HRID 2239907Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.C(N1CCCC(NC2C=C(N(CC3C=CC(OC)=CC=3)C3C=CC=CC=3)C3N(C(C#N)=CN=3)N=2)C1)C1C=CC=CC=1.[C@H:66]1([NH2:73])[CH2:71][CH2:70][C@H:69]([NH2:72])[CH2:68][CH2:67]1>C(Cl)Cl>[NH2:72][C@H:69]1[CH2:70][CH2:71][C@H:66]([NH:73][C:2]2[CH:3]=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[C:5]3[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:67][CH2:68]1

Participants

Conditions

Temperature: 165 °C

Procedure

In a 2 dram vial was added 4-(6-chloro-3-cyanoimidazo[1,2-b]pyridazin-8-ylamino)-N-methylbenzenesulfonamide (0.025 g, 0.069 mmol) from (1b) and (trans)-cyclohexane-1,4-diamine (0.700 g, 6.13 mmol). The mixture was heated to 165° C. for 1 hour. Upon cooling, The mixture was diluted with CH2Cl2, then washed with water, dried over Na2SO4, filtered, concentrated and purified by HPLC to provide the titled compound (0.008 g, 26.4% yield). 1H NMR (400 MHz, MeOD) δ ppm 7.91-7.99 (1H, s), 7.82-7.88 (2H, m), 7.48-7.55 (2H, m), 6.42-6.56 (1H, s), 3.68-3.84 (1H, m), 3.06-3.21 (1H, m), 2.49-2.59 (3H, s), 2.23-2.38 (2H, m), 2.04-2.17 (2H, m), 1.48-1.66 (2H, m), 1.28-1.45 (2H, m). LC/MS, m/z 441 (M+1). HPLC Rt, 2.30 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

temperatureUpon cooling
washwashed with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-b6fa90974bd1493e96fa0054c57639ba
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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