HCID 131732817, compound → HCID 89525913, compound

HRID 571377Notes

Reaction equation

HRID 571377 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH:17]C(=O)OCCCC)=[CH:16][C:11]=3[N:10]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:9]=2)=[CH:4][CH:3]=1>Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH2:17])=[CH:16][C:11]=3[N:10]([C:25]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131732817HCID 131732817, compound

Product 1

HCID 89525913HCID 89525913, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tent-Butyl (3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (403 mg, 0.706 mmol) was dissolved in HCl (4 M in dioxane, 6 mL) and stirred at room temperature for four hours. The reaction mixture was diluted with ethyl acetate and washed with NaOH (1 N) and brine. The aqueous layer was reextracted with 3:1 chloroform/IPA and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (359.1 mg, 0.672 mmol, 95%), which was carried onto the next step without further purification. MS ESI calc'd. For C31H23FN4 [M+1]+ 471, found 471.

Workup

  1. washwashed with NaOH (1 N) and brine
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-999bca31bb834763b68fef3e9610ef75
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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