Benzamide → HCID 178508349, compound

HRID 646756Notes

Reaction equation

C(N)(=O)C1C=CC=CC=1.[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:19]2[CH:20]=[C:21]([CH:34]=[CH:35][CH:36]=2)[C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[F:33])=[O:23])=[N:15][C:16]=1[C:17]#[N:18].[NH:37]([C:39]([C@H:41]1[CH2:46][CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42]1)=O)[NH2:38]>O>[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:19]2[CH:20]=[C:21]([CH:34]=[CH:35][CH:36]=2)[C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[F:33])=[O:23])=[N:15][C:16]=1[C:17]1[NH:38][N:37]=[C:39]([CH:41]2[CH2:46][CH2:45][CH2:44][NH:43][CH2:42]2)[N:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

3-(5-anmino-6{3-[(3S)-piperidin-3-yl]-1H-1,2,4-traiazol-5-yl}pyrazine-2-yl)-N[4-chloro-2-fluorophenyl)methyl]benzamide: 3-(5-Amino-6-cyano-pyrazin-2-yl)-N-(4-chloro-2-fluoro-benzyl)-benzamide (238.0 mg, 0.63 mmol) and 1,1-dimethylethyl (3S)-3-(hydrazinocarbonyl)piperidine-1-carboxylate (460 mg, 1.89 mmol) was combined together and it was heated to 180° C. for 1 or 2 hrs. The reaction mixture was poured into water (575 mL), and extracted with ethyl acetate (2×35 mL) then dried over anhydrous sodium sulfate and filteration, concentration and purified by MPLC to give 3-[5-amino-6-(5-piperidin-3-yl-2H-[1,2,4]triazol-3-yl)-pyrazin-2-yl]-N-(4-chloro-2-fluoro-benzyl)-benzamide (206.0 mg, 65.0% yield): 1H NMR (400 MHz, d4-MeOH): δ 8.60 (d, 2H), 8.20 (d, 1H), 7.82 (d, 1H), 7.58 (t, 1H), 7.38 (t, 1H), 7.15 (m, 2H), 4.60(s, 2H), 3.62 (m, 1H), 3.40(m, 3H), 2.99 (m, 1H), 2.37 (m, 1H), 1.98 (m, 3H); MS (EI) for C25H24N8OFCl: 507.03 (MH+).

Workup

extractionextracted with ethyl acetate (2×35 mL)
dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
custompurified by MPLC

Sources & evidence

ORD record: ord-8f59ec093b6a42f381aea718e55f32db
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704995B2

Reaction notes

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