Hydrochloric Acid → Tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate

HRID 624736Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:5]2[N:22]=[CH:23][CH:24]=[C:4]2[N:3]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29].Cl.O1CCOCC1.[OH-].[Na+]>O.C(O)(C)(C)C>[Cl:25][C:26]1[CH:27]=[C:28]([NH:29][C:2]2[CH:7]=[C:6]([NH:8][C:9]3[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=3)[C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[N:5]3[N:22]=[CH:23][CH:24]=[C:4]3[N:3]=2)[CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the reaction flask, tert-butyl 3-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate (2.9 g, 8.2 mmol) was added along with 3-chloroaniline (2.2 mL, 20.6 mmol), 4N HCl in dioxane (2.6 mL, 10.4 mmol), and t-butyl alcohol (41 mL). The reaction was stirred at 100° C. for 2 days then cooled to room temperature. The mixture was diluted with water, made basic with 3N NaOH, filtered and washed with water. The product, tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate, was collected as a solid in 55% yield after drying under vacuum overnight. LCMS (M+1=436)

Workup

temperaturethen cooled to room temperature
filtrationfiltered
washwashed with water
customThe product, tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate, was collected as a solid in 55% yield
customafter drying under vacuum overnight

Sources & evidence

ORD record: ord-cd611ddcb5814b5cbe9822c9636c0585
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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