Hydrochloric Acid → HCID 178479712, compound

HRID 1711428Notes

Reaction equation

HRID 1711428 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([N:31]1[CH2:36][CH2:35][CH:34]([C:37](O)=[O:38])[CH2:33][CH2:32]1)(OC(C)(C)C)=O.[ClH:40].C(N=C=N)C.C(O)(C(F)(F)F)=O.Cl>CC#N.CO.C(Cl)(Cl)Cl>[ClH:40].[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH:23][C:37]([CH:34]4[CH2:35][CH2:36][NH:31][CH2:32][CH2:33]4)=[O:38])[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 21883477Ethylcarbodiimide hydrochlorideHCID 178507365HCID 178507365, compound

Product 1

HCID 178479712HCID 178479712, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(1-naphthylsulfonyl)-1H-indazol-5-amine (300 mg, 0.928 mmol), 1-Boc-piperidine-4-carboxylic acid (276 mg, 1.21 mmol), 1-[3-(dimethylamino)propyl)]-3-ethylcarbodimide hydrochloride (231 mg, 1.21 mmol) in CH3CN was stirred at room temperature overnight and concentrated to dryness to provide a residue. The residue was treated with TFA at room temperature for 2 hours and concentrated to dryness in vacuo. The resultant residue was purified by reverse phase HPLC to give a solid. The solid was dispersed in methanol and chloroform, treated with aqueous HCl solution, concentrated and dried in vacuo to provide the title compound as a milky light orange solid, characterized by HNMR and mass spectral analyses, MS (ES+) m/e 435 (MH+).

Workup

  1. concentrationconcentrated to dryness
  2. customto provide a residue
  3. concentrationconcentrated to dryness in vacuo
  4. customThe resultant residue was purified by reverse phase HPLC
  5. customto give a solid
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-df96d461ff804246993d4d40687c3ef9
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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