Dimethylformamide → HCID 118094001, compound

HRID 515539Notes

Reaction equation

Br[C:2]1[C:3](=[O:28])[NH:4][C:5]2[CH:6]=[C:7]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:8]=[C:9]([S:12]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:14])=[O:13])[C:10]=2[CH:11]=1.[CH3:29][N:30](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([C:2]1[C:3](=[O:28])[NH:4][C:5]2[CH:6]=[C:7]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:8]=[C:9]([S:12]([NH:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)(=[O:14])=[O:13])[C:10]=2[CH:11]=1)#[N:30]

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 3-bromo-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydroquinoline-5-sulfonamide (16 mg, 0.034 mmol), zinc cyanide (20 mg, 5 equiv), Pd(PPh3)4 (4 mg, 10 mol %) and DMF was heated at 135° C. for 2 hours. The reaction mixture was purified by preparative HPLC to give 3-cyano-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydroquinoline-5-sulfonamide.

Workup

customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-e8ed9e27769c4b49be285ed7d61b3890
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108953B2

Reaction notes

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