Dimethylacetamide → HCID 135870675, compound

HRID 1847232Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[C:5]([OH:18])=[C:6]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][S:8][C:7]=12.C[C:27]([N:29](C)C)=O>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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2].[Zn]>[C:27]([C:2]1[N:3]=[C:4]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[C:5]([OH:18])=[C:6]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][S:8][C:7]=12)#[N:29]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of {[7-bromo-3-(4-fluoro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carbonyl]-amino}-acetic acid (105 mg, 0.246 mmol), Pd2(dba)3 (22.5 mg, 0.0246 mmol), dppf (27.2 mg, 0.0492 mmol), Zn(CN)2 (28.9 mg, 0.246 mmol), Zn dust (1.6 mg, 0.0246 mmol), and DMA (0.49 mL) was stirred at 120° C. for 1 h. After cooling to r.t. the mixture was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Elution with 0-20% MeOH/CH2Cl2/0.1% HCOOH gave the title compound as a white solid (21.8 mg): MS (m/z) 371.1 (M−1).

Workup

temperatureAfter cooling to r.t. the mixture
concentrationwas concentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel
washElution with 0-20% MeOH/CH2Cl2/0.1% HCOOH

Sources & evidence

ORD record: ord-90b04fad90704291a52371fc0203bf59
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952160B2

Reaction notes

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