Hydrochloric Acid → HCID 57863466, compound

HRID 1446753Notes

Reaction equation

HRID 1446753 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:51])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([NH:25][C:26](=[O:50])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[N:38]5[CH:39]=[CH:40][C:41]([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=6)=[CH:42][C:37]5=[N:36][CH:35]=4)=[CH:30][C:29]=3[F:49])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.CO.C1COCC1>[F:49][C:29]1[CH:30]=[C:31]([C:34]2[N:38]3[CH:39]=[CH:40][C:41]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)=[CH:42][C:37]3=[N:36][CH:35]=2)[CH:32]=[CH:33][C:28]=1[CH2:27][C:26]([NH:25][C:17]1[CH:18]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:20]=[C:15]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:51])[CH:16]=1)=[O:50]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68546091HCID 68546091, compound

Product 1

HCID 57863466HCID 57863466, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Dissolve 4-(3-{2-[2-fluoro-4-(7-pyridin-2-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetylamino}-5-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (0.76 g, 0.108 mmol) in 1:1 CH2Cl2 MeOH (20 mL) and add 2M HCl in THF (2 mL), then stir 2 hours and concentrate in vacuo. Load onto a Varian MegaElut® SCX cartridge (10 gram cartridge prewashed with methanol), rinse with methanol to remove impurities then elute crude product with 2 M NH3 in methanol. Concentrate this solution in vacuo then purify by silica gel chromatography (0%→10% 2 M NH3 Methanol:DCM) to give a yellow residue (0.400 g, 49% over 2 steps). MS (ES), m/z 603 (M+1).

Workup

  1. concentrationconcentrate in vacuo
  2. washLoad onto a Varian MegaElut® SCX cartridge (10 gram cartridge prewashed with methanol), rinse with methanol
  3. customto remove impurities
  4. washthen elute crude product with 2 M NH3 in methanol
  5. concentrationConcentrate this solution in vacuo
  6. customthen purify by silica gel chromatography (0%→10% 2 M NH3 Methanol:DCM)
  7. customto give a yellow residue (0.400 g, 49% over 2 steps)

Sources & evidence

ORD record
ord-feb40baddf73499582849aa638c2d5bc
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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