Dimethylacetamide → HCID 135870675, compound

HRID 1050759Notes

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-d64f2b0d163445ecb7ee8bf58300591c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09387200B2

Reaction notes

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