HCID 178454362, compound → HCID 178461208, compound

HRID 1852862Notes

Reaction equation

HRID 1852862 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:24][C@H:25]4[CH2:30][CH2:29][C@H:28]([CH3:31])[CH2:27][CH2:26]4)[C:15]([N:17]4[CH2:21][CH2:20][CH2:19][C@H:18]4[CH2:22][F:23])=[N:16][C:12]=3[CH:11]=[C:10]([C:32](=[NH:42])[NH:33][NH:34][C:35](OC(C)(C)C)=[O:36])[N:9]=2)[CH:5]=[N:6][CH:7]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:24][C@H:25]4[CH2:26][CH2:27][C@H:28]([CH3:31])[CH2:29][CH2:30]4)[C:15]([N:17]4[CH2:21][CH2:20][CH2:19][C@H:18]4[CH2:22][F:23])=[N:16][C:12]=3[CH:11]=[C:10]([C:32]3[NH:42][C:35](=[O:36])[NH:34][N:33]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 178454362HCID 178454362, compound

Product 1

HCID 178461208HCID 178461208, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of crude tert-butyl 2-((4-(5-chloropyridin-3-yl)-2-((S)-2-(fluoromethyl)pyrrolidin-1-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)(imino)methyl)hydrazinecarboxylate (19.0 mg, 0.032 mmol) in acetonitrile (793 μL) was stirred at 80° C. for 72 hr. Purification of the reaction by mass triggered reverse phase HPLC (C-18), eluting with acetonitrile/water containing 0.1% TFA afforded 5-{4-(5-chloropyridin-3-yl)-2-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-2,4-dihydro-3H-1,2,4-triazol-3-one (TFA salt). 1H NMR (600 MHz, CD3OD) δ 8.83 (d, J=1.8 Hz, 1H), 8.72 (d, J=2.3 Hz, 1H), 8.38 (t, J=2.1 Hz, 1H), 7.96 (s, 1H), 4.70 (dd, J=3.3, 9.9 Hz, 0.5H), 4.65-4.51 (m, 2H), 4.45 (dd, J=4.1, 9.9 Hz, 0.5H), 3.90 (dd, J=8.4, 14.9 Hz, 1H), 3.85-3.74 (m, 2H), 3.55 (dd, J=6.0, 14.9 Hz, 1H), 2.32-2.24 (m, 1H), 2.19-2.11 (m, 1H), 2.05-1.93 (m, 2H), 1.50-1.42 (m, 2H), 1.27-1.19 (m, 1H), 1.15-1.04 (m, 1H), 1.04-0.97 (m, 1H), 0.73 (d, J=6.6 Hz, 3H), 0.72-0.63 (m, 1H), 0.63-0.50 (m, 4H). MS ESI calc'd. for C26H30ClFN8O [M+H]+ 525. found 525.

Workup

  1. customPurification of the reaction by mass triggered reverse phase HPLC (C-18)
  2. washeluting with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-3550cf12050f496493c1798644ddd7a4
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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