HCID 178459708, compound → HCID 59856707, compound

HRID 1036781Notes

Reaction equation

HRID 1036781 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([C:20](=[NH:23])[NH:21]O)=[C:18]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:26]=3[F:35])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]>CC([O-])=O.[Zn]>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([C:20](=[NH:21])[NH2:23])=[C:18]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:26]=3[F:35])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 178459708HCID 178459708, compound

Product 1

HCID 59856707HCID 59856707, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 175AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-[6-(2-Fluoro-4-methanesulfonyl-phenylamino)-5-(N-hydroxycarbamimidoyl)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (0.510 g, 0816 mmol) was dissolved in acetic acid glacial (20 mL) and zinc dust (1 g, 16.32 mmol) was added. The reaction mixture was heated at 70° C. for 40 min. The crude was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by HPLC to afford Compound A100 (43 mg, 8.65%). Exact mass calculated for C21H27FN6O5S 494.17, found 495.5 (MH+).

Workup

  1. filtrationThe crude was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by HPLC
  4. customto afford Compound A100 (43 mg, 8.65%)

Sources & evidence

ORD record
ord-af6fe374b1b046c6955620124b95de94
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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