Hydrochloric Acid → HCID 67240477, compound

HRID 1949431Notes

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-7ff402e014454b9d9d507727f3a703b1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399681B2

Reaction notes

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