Hydrochloric Acid → HCID 57798921, compound

HRID 2100421Notes

Reaction equation

HRID 2100421 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]([N:31]4[CH2:40][CH2:39][C:34]5(OCC[O:35]5)[CH2:33][CH2:32]4)=[O:30])[CH:23]=3)=[O:13])[CH:7]=[CH:8]2)=[N:3]1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]([N:31]4[CH2:32][CH2:33][C:34](=[O:35])[CH2:39][CH2:40]4)=[O:30])[CH:23]=3)=[O:13])[CH:7]=[CH:8]2)=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23120475HCID 23120475, compound

Product 1

HCID 57798921HCID 57798921, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,4-Dioxa-8-aza-spiro[4.5]decan-8-carboxylic acid(4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (564 mg, 1.04 mmol) in acetone (35 mL), was cooled to 4° C. and treated dropwise with aqueous hydrochloric acid (4 N, 9 mL). The reaction was warmed to rt and stirred overnight. The reaction was made basic by the addition of saturated aqueous sodium hydrogencarbonate and extracted with EtOAc. The organic phase was washed with brine, dried, filtered and concentrated in vacuo to give 4-oxo-piperidine-1-carboxylic acid (4-{[2-(2-methyl-2H-indazol-6-ylcarbamoyl)-phenylamino]-methyl}-pyridin-2-yl)-amide (467 mg, 90%) as a solid; 1H-NMR (300 MHz, d6-DMSO) 10.14 (1H, s), 9.36 (1H, s), 8.25 (1H, s), 8.17 (1H, d), 8.10 (1H, s), 7.96 (1H, t), 7.86 (1H, s), 7.72 (1H, d), 7.64 (1H, d), 7.23-7.32 (2H, m), 6.96-6.98 (1H, m), 6.66 (1H, t), 6.55 (1H, d), 4.45 (2H, d), 4.13 (3H, s), 3.72-3.76 (4H, m), 2.36-2.40 (4H, m); m/z (ES+) 498 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d897f506d5e5455f9d158a9e66142fec
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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