HCID 44125257, compound → HCID 44125254, compound

HRID 1162483Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([CH:14]=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:21][S:22](C1C=CC(C(O)(C)C)=CC=1)(=[O:24])=[O:23].CC1(C)C(C)(C)OB(C2C=CC3N(C=C(NC(=O)C)N=3)N=2)O1.BrC1C=C(NS([N:69]2[CH2:74][CH2:73][O:72][CH2:71][CH2:70]2)(=O)=O)C(Cl)=NC=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([CH:14]=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:21][S:22]([N:69]1[CH2:74][CH2:73][O:72][CH2:71][CH2:70]1)(=[O:23])=[O:24]

Participants

Reactant 3

HCID 44125257HCID 44125257, compound

HCID 57749440N-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HCID 59519519HCID 59519519, compound

Product 1

HCID 44125254HCID 44125254, compoundYield 26%

Procedure

Following the procedure described for compound N-(6-(6-chloro-5-(4-(2-hydroxypropan-2-yl)phenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 35), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (122 mg, 404 μmol) (Example 35, Step 3) was reacted with N-(5-bromo-2-chloropyridin-3-yl)morpholine-4-sulfonamide from Step 1 (120 mg, 336 μmol) to afford the title compound as a light green solid (40 mg, 26% yield). MS (ESI positive ion) m/z: 452 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.12 (s, 3H), 3.12-3.18 (m, 4H), 3.60-3.68 (m, 4H), 7.86 (d, J=9.39 Hz, 1H), 8.14 (d, J=9.39 Hz, 1H), 8.33 (s, 1H), 8.54 (d, J=2.15 Hz, 1H), 8.90 (s, 1H), 10.14 (s, 1H), 10.97 (s, 1H).

Sources & evidence

ORD record: ord-f71c3a93233845039c62049f3c3564ca
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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