Trifluoroacetic acid → tert-butyl 9-((5-chloro-2-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1478056Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:26][CH2:25][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[CH:28]1([CH2:31][N:32]2[CH:36]=[C:35]([NH2:37])[CH:34]=[N:33]2)[CH2:30][CH2:29]1.FC(F)(F)C(O)=O>O1CCOCC1>[Cl:27][C:5]1[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]3)[CH2:25][CH2:26]2)=[N:7][C:2]([NH:37][C:35]2[CH:34]=[N:33][N:32]([CH2:31][CH:28]3[CH2:30][CH2:29]3)[CH:36]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 9-[(2,5-dichloropyrimidin-4-yl)amino]-3-azaspiro[5.5]undecane-3-carboxylate (500.5 mg, 1.21 mmol) and 1-(cyclopropylmethyl)-1H-pyrazol-4-amine (330.5 mg, 2.41 mmol) in 1,4-dioxane (50 mL) was added trifluoroacetic acid (686.5 mg, 6.02 mmol). The mixture was stirred at 100° C. overnight and concentrated in vacuo. The residue was purified with a silica gel column chromatography (PE/EtOAc (v/v)=1/1 to DCM/MeOH (v/v)=7/1) to give the product as a light yellow solid (550 mg, 88.45%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified with a silica gel column chromatography (PE/EtOAc (v/v)=1/1 to DCM/MeOH (v/v)=7/1)

Sources & evidence

ORD record: ord-a724ccd8a0bb49298fcb8bdd57377a3a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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