Methylamine → HCID 10146154, compound

HRID 2229208Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([CH2:8][C:9]2[N:13]3[N:14]=[C:15](Cl)[CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:19][N:20]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[C:24]=2[Cl:33])=[O:22])[CH:7]=1.[CH3:41][NH2:42].C1COCC1>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([CH2:8][C:9]2[N:13]3[N:14]=[C:15]([NH:42][CH3:41])[CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:19][N:20]([CH2:34][CH2:35][CH:36]([CH3:37])[CH3:38])[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[C:24]=2[Cl:33])=[O:22])[CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 130 mg (0.2 mmol) N-({3-[(5-bromo-2-methoxyphenyl)methyl]-6-chloro(imidazolo[1,2-b]pyridazin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in DMSO (3 mL) is treated with 2M methyl amine in THF 1.5 mL (3.0 mmol). The reaction mixture is heated to 150° C. in a sealed tube for 18 hr and following cooling partitioned between ethyl acetate and water. The organic extract is washed with 5×10 mL water, dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude residue. The residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford 31 mg (24%) of the title compound. Mass Spec m/z (M++1) 646.

Workup

temperaturefollowing cooling
custompartitioned between ethyl acetate and water
extractionThe organic extract
washis washed with 5×10 mL water
dry with materialdried over anhydrous MgSO4
customthe solvent removed in vacuo
customto give the crude residue
customThe residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH)

Sources & evidence

ORD record: ord-a6cca5edc52249c8a5673e06a497cd7e
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420365B1

Reaction notes

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