Ammonia → HCID 57977430, compound

HRID 1866090Notes

Reaction equation

[NH3:1].[Cl:2][C:3]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH3:14])=[C:7]([NH:15][CH:16]([CH3:20])[CH:17]([CH3:19])[CH3:18])[N:6]2[N:21]=[CH:22][C:23]([C:24](Cl)=[O:25])=[C:5]2[N:4]=1.C(OCC)(=O)C>O1CCCC1>[Cl:2][C:3]1[C:8]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH3:14])=[C:7]([NH:15][CH:16]([CH3:20])[CH:17]([CH3:19])[CH3:18])[N:6]2[N:21]=[CH:22][C:23]([C:24]([NH2:1])=[O:25])=[C:5]2[N:4]=1

Participants

Conditions

Temperature: 22 °C

Procedure

At room temperature, 15 ml of concentrated aqueous ammonia were added to 4.0 g (10 mmol) of 5-chloro-7-(1,2-dimethylpropylamino)-6-(3-methylthiophen-2-yl)pyrazolo[1,5-α]pyrimidine-3-carbonyl chloride in 30 ml of tetrahydrofuran. The mixture was stirred at 22° C. for 16 hours, and 50 ml of ethyl acetate were then added. The organic phase was separated off, dried over sodium sulphate and concentrated under reduced pressure. This gave 3.0 g of 5-chloro-7-(1,2-dimethyl-propylamino)-6-(3-methylthiophen-2-yl)pyrazolo[1,5-α]pyrimidine-3-carboxamide (logPs=3.5; content according to HPLC: 94%)

Workup

customThe organic phase was separated off
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-476ce1549c934963a5668a29e22f28d8
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629294B2

Reaction notes

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