Aniline → HCID 57917317, compound

HRID 69179Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)=[CH:16][N:17]=3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1.NC1C=CC=CC=1.ClC1C=C(C=CC=1)N>>[C:4]1([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)=[CH:16][N:17]=3)[N:14]=2)[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 6115Aniline

HCID 79323-Chloroaniline

HCID 57917421(3-Chloro-phenyl)-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-amine

Product 1

HCID 57917317HCID 57917317, compound

Procedure

The title compound was prepared in analogy to the compound of Example 121 using aniline as starting material instead of 3-chloroaniline and with a preparative LCMS purification instead of a flash chromatography (tR 4.30 min (conditions 4), MH+=352.3, 1H-NMR in DMSO-d6: 8.91 (m, 1H); 8.36 (m, 1H); 8.17 (d, 1H); 8.08 (s, 1H); 8.03 (d, 1H); 7.96 (m, 1H); 7.79 (m, 1H); 7.58 (dd, 1H); 7.50 (m, 2H); 7.35 (d, 1H); 7.25 (t, 2H); 7.01 (t, 1H); 4.59 (s, 2H)).

Workup

customwith a preparative LCMS purification instead of a flash chromatography (tR 4.30 min (conditions 4), MH+=352.3, 1H-NMR in DMSO-d6: 8.91 (m, 1H); 8.36 (m, 1H); 8.17 (d, 1H); 8.08 (s, 1H); 8.03 (d, 1H); 7.96 (m, 1H); 7.79 (m, 1H); 7.58 (dd, 1H); 7.50 (m, 2H); 7.35 (d, 1H); 7.25 (t, 2H); 7.01 (t, 1H); 4.59 (s, 2H))

Sources & evidence

ORD record: ord-83372ea55fab41b5b6b07391a57a134b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822468B2

Reaction notes

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