Trifluoroacetic acid → Trifluoroacetic acid

HRID 571510Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([CH2:10][C:11]1([N:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]4[NH:33][CH:34]=[CH:35][C:28]=34)[CH:24]=[N:23]2)[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1)#[N:9]>C(Cl)Cl>[NH:33]1[C:29]2=[N:30][CH:31]=[CH:32][C:27]([C:25]3[CH:24]=[N:23][N:22]([C:11]4([CH2:10][C:8]#[N:9])[CH2:12][NH:13][CH2:14]4)[CH:26]=3)=[C:28]2[CH:35]=[CH:34]1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

Conditions

Temperature: 30 °C

Procedure

Trifluoroacetic acid (7.0 mL) was added to tert-butyl 3-(cyanomethyl)-3-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (0.90 g, 2.4 mmol) in methylene chloride (7.0 mL). The reaction mixture was stirred at 30° C. for 2 h. The volatiles were removed under reduced pressure to afford the desired product (quantitative) as TFA salt which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=279.1.

Workup

customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-aae912e477fa40e4a721488ca9cc54f6
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023840B2

Reaction notes

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