3-Chloroaniline → HCID 53240562, compound

HRID 624692Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>O1CCOCC1>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[CH:7]=[C:6]([NH:8][CH:9]3[CH2:11][CH2:10]3)[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]3[N:3]=2)[CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (177 mg, 0.75 mmol) in 1,4-dioxane was added 3-chloroaniline (397 μl, 3.75 mmol). The mixture was heated in microwave at 120° C. for 60 minutes. The precipitate was filtered off, and the filtrate was purified by prep TLC (1% MeOH/DCM) to yield 26 mg (11% yield) of 5-(3-chlorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. LCMS (M+1=328)

Workup

filtrationThe precipitate was filtered off
customthe filtrate was purified by prep TLC (1% MeOH/DCM)

Sources & evidence

ORD record: ord-232a38f071f94895b6894fdbb82c750a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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