HCID 178490953, compound → HCID 178505052, compound

HRID 1943430Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([N:28](CC3C=CC(OC)=CC=3)[S:29]([CH3:32])(=[O:31])=[O:30])[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[F:27])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[C:12]3[N:13]([C:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[F:27])=[O:19])=[CH:16][N:17]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-(trans-4-aminocyclohexylamino)-N-(3-fluoropyridin-4-yl)-8-(N-(4-methoxybenzyl)methylsulfonamido)imidazo[1,2-b]pyridazine-3-carboxamide (30 mg, 0.037 mmol) in TFA (1 mL) was heated to 80° C. for 1.5 h. The reaction mixture was concentrated and evaporated from DCM/MeOH to give 20B (26 mg, 102%) as a white solid. [M+H]=463. HPLC Peak Rt=1.758 minutes. (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm.)

Workup

concentrationThe reaction mixture was concentrated
customevaporated from DCM/MeOH

Sources & evidence

ORD record: ord-1d0cbbfacf784069a7366c8cb333694a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389527B2

Reaction notes

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