Diisopropylethylamine → HCID 86711210, compound

HRID 1850793Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[CH2:9][C@H:8]2[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]1.Br[C:14]1[N:22]=[C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:16]2[N:15]=1.CCN(C(C)C)C(C)C>C(O)C>[N:15]1[N:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]2=[N:22][C:14]=1[N:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[CH2:9][C@H:8]2[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol (Intermediate 11; 70 mg, 0.4 mmol) and 2-bromo[1,2,4]triazolo[1,5-a]pyrimidine (9 mg, 0.496 mmol) in ethanol (2 mL) was added DIEA (0.22 mL, 1.21 mmol) and the resulting mixture heated via microwave to 120° C. for 1 hr. HPLC of the reaction mixture proved the reaction was complete with the absence of Intermediate 11. The mixture was filtered (glass wool filter paper, Whatman 1821 110), and washed with ethanol. The filtrate was concentrated to dryness under reduced pressure and the resulting residue purified via preparative TLC plates (2×1000 μM silica gel) eluting with 50% ethyl acetate in hexane. The product was removed from the silica gel by extracting with ethyl acetate and the solvent was removed under reduced pressure to afford the title compound as an off-white solid. MS (Multimode) m/z 288 [M+H]+.

Workup

filtrationThe mixture was filtered
filtration(glass wool filter paper, Whatman 1821 110)
washwashed with ethanol
concentrationThe filtrate was concentrated to dryness under reduced pressure
customthe resulting residue purified via preparative TLC plates (2×1000 μM silica gel)
washeluting with 50% ethyl acetate in hexane
customThe product was removed from the silica gel
extractionby extracting with ethyl acetate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-4f639b887703481c9d16189af27e5ef4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957062B2

Reaction notes

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