Hydrochloric Acid → HCID 67240477, compound

HRID 2384692Notes

Reaction equation

N#N.[Cl:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[C:19]4[S:23][C:22]([N:24]5[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]5)=[N:21][C:20]4=[O:31])=[CH:15][CH:16]=3)[CH:11]=[N:10]2)=[C:6](I)[CH:5]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.C([Sn](CCCC)(CCCC)[C:61]([O:63]CC)=[CH2:62])CCC.Cl>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[C:61]([C:6]1[CH:5]=[C:4]([Cl:3])[CH:33]=[CH:32][C:7]=1[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[C:19]3[S:23][C:22]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)=[N:21][C:20]3=[O:31])=[CH:15][CH:16]=2)[CH:11]=[N:10]1)(=[O:63])[CH3:62]

Participants

Conditions

Temperature: 90 °C

Procedure

To a N2 flushed vial was added 5-[1-(4-chloro-2-iodo-benzyl)-1H-indazol-5-ylmethylene]-2-(4-methyl-piperazin-1-yl)thiazol-4-one (100 mg, 0.15 mmol), Pd2(dba)3 (10 mg, 0.011 mmol), biphenyl-2-yl-di-t-butyl-phosphane (12 mg, 0.04 mmol), Tributyl-(1-ethoxy-vinyl)-stannane (86 mg, 0.23 mmol) and dioxane (2 mL). The resulting mixture was heated at 90° C. for 16 h. The resulting mixture was poured into water and extracted with EtOAc. The organic layer was dried and concentrated, and the residue was purified by preparative HPLC to yield a white solid which was treated 1 N hydrochloric acid in MeOH to yield the title compound.

Workup

extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated
customthe residue was purified by preparative HPLC
customto yield a white solid which

Sources & evidence

ORD record: ord-6ac1fa30c91d42ff9f0cba5c9ba004cb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263781B2

Reaction notes

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