Chloride → HCID 131726109, compound

HRID 723994Notes

Reaction equation

HRID 723994 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[N:15][N:16]4[CH:21]=[C:20]([NH:22]C(=O)OC(C)(C)C)[CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-:37]>ClCCl.CCOCC>[ClH:37].[ClH:37].[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)=[N:15][N:16]4[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 312ChlorideHCID 131726106HCID 131726106, compound

Product 1

HCID 131726109HCID 131726109, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-6-ylcarbamate (35 mg, 0.072 mmol) in dichloromethane was addedhydrogen chloride (144 μL, 4 N in dioxane, 0.58 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ether and the precipitated solids were collected on a filter to provide 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-6-amine dihydrochloride (9 mg, 27%) as a brownish yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.25 (br, 1H), 7.97–7.91 (m, 2H), 7.53 (m, 2H), 7.26 (t, 2H), 7.06 (d, 1H), 6.15 (br, 1H), 4.14–3.85 (br, 1H), 1.85 (br, 2H), 1.65 (br, 2H), 1.48 (br, 4H); MS m/z 389 (M+1).

Workup

  1. customthe precipitated solids were collected on
  2. filtrationa filter

Sources & evidence

ORD record
ord-84396535f40f48e2bb034968341bed67
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

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