Triethylamine → HCID 59464038, compound

HRID 1713768Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:21][CH:22]=2)=[O:15])=[N:11][N:10]=1.[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1.C(N(CC)CC)C>CC(N(C)C)=O>[CH:29]1([CH2:32][N:26]2[CH2:27][CH2:28][N:23]([C:20]3[N:19]=[CH:18][C:17]([NH:16][C:14]([C:12]4[O:13][C:9]([NH:8][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])=[N:10][N:11]=4)=[O:15])=[CH:22][CH:21]=3)[CH2:24][CH2:25]2)[CH2:31][CH2:30]1

Participants

Conditions

Temperature: 110 °C

Procedure

5-[(2-Fluorophenyl)amino]-N-(6-piperazin-1-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide (Intermediate 41) (120 mg, 0.31 mmol) in DMA (2 mL) was placed in a microwave tube with cyclopropylmethyl bromide (88 mg, 0.62 mmol), and triethylamine (64 mg, 0.62 mmol). The mixture was heated with stirring in the microwave at 110° C. for 60 minutes then transferred directly onto a reverse phase HPLC column and eluted with a gradient of acetonitrile/water containing 0.2%/TFA to give the title compound (125 mg, 91%) as a solid; 1H NMR δ 10.65 (1H, s), 10.40 (1H, bs), 8.20 (1H, s), 7.65 (2H, m), 6.90 (2H, m), 6.80 (1H, m), 6.65 (1H, d), 4.00 (2H, d), 3.25 (2H, d), 2.80 (6H, m), 0.75 (1H, m), 0.30 (2H, m), 0.00 (2H, m); MS m/e MH+ 438.

Workup

temperatureThe mixture was heated
washeluted with a gradient of acetonitrile/water containing 0.2%/TFA

Sources & evidence

ORD record: ord-c29927375c064a20b0921d9fb173ae1d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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