Methane → N-{5-[(3-hydroxycyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide

HRID 2382860Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3]1.Cl[C:10]1[N:15]2[N:16]=[C:17]([NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=3)[N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C.C>CC(O)(C)C>[OH:8][CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH2:3]1

Participants

Conditions

Temperature: 200 °C

Procedure

3-amino-cyclohexanol (Betapharma, 67.33 mg; 0.58 mmol; 2.0 eq.) was added to a mixture of N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B4), 80 mg; 0.29 mmol; 1.0 eq.), DIEA (76 mg; 0.58 mmol; 2.0 eq.) and activated Charcoal (8 mg) in tBuOH (0.8 mL). The reaction mixture was heated at 200° C. for 2×30 min under microwave irradiation. After this time, it was filtered on a celite pad and the cake was washed with ACN. The filtrate was directly purified by RP-HPLC (Starting with 15% ACN in water for 5 min, then up to 30% in 10 min.). The title compound was isolated after lyophilisation as a white powder (51 mg, 49%). HPLC, Rt: 2.14 min. (purity 98.0%). LC/MS, M+(ESI): 353.0, M−(ESI): 351.0.

Workup

filtrationAfter this time, it was filtered on a celite pad
washthe cake was washed with ACN
customThe filtrate was directly purified by RP-HPLC (
waitup to 30% in 10 min.)

Sources & evidence

ORD record: ord-e22c6258d9b947909432049846c728d5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263595B2

Reaction notes

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