Hydrochloric Acid → 1-[4-(9-Fluoro-3-phenylpyrimido[1,2-b]indazole-2-yl)phenyl]-cyclobutylamine

HRID 877052Notes

Reaction equation

HRID 877052 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[C:26]([F:29])[CH:25]=[CH:24]5)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]2[C:28](=[C:20]3[N:19]=[C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:8]5([NH2:7])[CH2:9][CH2:10][CH2:11]5)=[CH:17][CH:16]=4)[C:31]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:30][N:21]3[N:22]=2)[CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86702529HCID 86702529, compound

Product 1

HCID 573777651-[4-(9-Fluoro-3-phenylpyrimido[1,2-b]indazole-2-yl)phenyl]-cyclobutylamineYield 38.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In a second experiment 420 mg (0.83 mmol) {1-[4-(9-fluoro-3-phenylpyrimido[1,2-b]indazole-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester, after dissolution in 5 mL dioxane, were treated with 22 mL 4M hydrogen chloride in dioxane. The reaction mixture was worked up as described for the first experiment. The crude products of both experiments were purified by joint chromatography on amine silicagel (eluents: dichoromethane/methanol) yielding 129.5 mg of the desired product.

Workup

  1. customThe crude products of both experiments were purified by joint chromatography on amine silicagel (eluents: dichoromethane/methanol)

Sources & evidence

ORD record
ord-591650d5eb1047fdb392c2f6e2e604ce
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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