Hydrazine → HCID 178432100, compound

HRID 1992078Notes

Reaction equation

[C:1]([N:3]=[C:4]([N:12]1[CH2:17][CH2:16][C:15]([CH2:24][CH2:25][N:26]2[CH:31]3[CH2:32][CH2:33][CH:27]2[CH2:28][CH:29]([N:34]2[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[N:36]=[C:35]2[CH3:43])[CH2:30]3)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)OC1C=CC=CC=1)#[N:2].[NH2:44][NH2:45]>C(O)(C)C>[CH3:43][C:35]1[N:34]([CH:29]2[CH2:30][CH:31]3[N:26]([CH2:25][CH2:24][C:15]4([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH2:16][CH2:17][N:12]([C:4]5[NH:45][N:44]=[C:1]([NH2:2])[N:3]=5)[CH2:13][CH2:14]4)[CH:27]([CH2:33][CH2:32]3)[CH2:28]2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate (18 mg, 0.031 mmol) in isopropyl alcohol (1 mL) was added hydrazine (3.6 μL, 0.11 mmol). The resulting mixture was then stirred at 80° C. for 4 hours. After evaporation of the solvents, the residue was purified by flash chromatography to afford 5-(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)-1H-1,2,4-triazol-3-amine as white solid (12.5 mg, 79%). 1H NMR (300 MHz, CDCl3) δ 7.67-7.64 (m, 2H), 7.39-7.29 (m, 5H), 7.25-7.13 (m, 3H), 4.66-4.55 (m, 2H), 4.28 (br, 2H), 3.56-3.49 (m, 3H), 3.27-3.21 (m, 4H), 2.57 (s, 3H), 2.42-2.22 (m, 4H), 1.96-1.82 (m, 9H), 1.64-1.62 (m, 2H). HRMS m/z (M+H)+ calcd: 511.3298, obsd: 511.3289.

Workup

customAfter evaporation of the solvents
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-20800c0d4eb4482983e474a19b97551b
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Reaction notes

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