Trifluoroacetic acid → 5-(3-Aminoazetidin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959412Notes

Reaction equation

C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19](Br)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.[NH:34]1[CH2:37][CH:36]([NH:38]C(=O)OC(C)(C)C)[CH2:35]1.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O>CN(C=O)C.C(OC(=O)C)C.ClCCl>[NH2:38][CH:36]1[CH2:37][N:34]([C:19]2[N:20]=[C:21]([C:22]3[O:23][C:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:25][N:26]=3)[C:16]([NH2:8])=[N:17][CH:18]=2)[CH2:35]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of tert-butyl N-tert butoxycarbonyl-5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-ylcarbamate (200 mg, 0.3858 mmol) and tert-butyl N-(azetidin-3-yl)carbamate (66.44 mg, 0.3858 mmol) and DIPEA (99.72 mg, 134.4 μL, 0.7716 mmol) in DMF (5 mL) was heated at 90° C. After this time, the reaction mixture was cooled to room temperature and diluted with ethylacetate (5 mL), washed with water (5 mL) and concentrated in vacuo to leave a solid. The solid was dissolved in dichloromethane (10 mL) and trifluoroacetic acid (1.319 g, 891.2 μL, 11.57 mmol) was added and the resulting solution stirred at room temperature for 1 hr. The reaction mixture was concentrated in vacuo to leave an oil. The oil was redissolved in dichloromethane and concentrated in vacuo to leave the product, which was used crude in the next step.

Workup

temperatureAfter this time, the reaction mixture was cooled to room temperature
washwashed with water (5 mL)
concentrationconcentrated in vacuo
customto leave a solid
concentrationThe reaction mixture was concentrated in vacuo
customto leave an oil
concentrationconcentrated in vacuo
customto leave the product, which

Sources & evidence

ORD record: ord-0d5afd3381054e59a165850b0ebf19e9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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