5-oxo-1,2,4-oxadiazoline → HCID 178461245, compound

HRID 81187Notes

Reaction equation

HRID 81187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:25][C@H:26]4[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]4)[C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])=[N:16][C:12]=3[CH:11]=[C:10]([C:33](=[NH:36])[NH:34][OH:35])[N:9]=2)[CH:5]=[N:6][CH:7]=1.[O:37]1[C:41](=O)NC=N1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:25][C@H:26]4[CH2:27][CH2:28][C@H:29]([CH3:32])[CH2:30][CH2:31]4)[C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])=[N:16][C:12]=3[CH:11]=[C:10]([C:33]3[NH:36][C:41](=[O:37])[O:35][N:34]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 1354247705-oxo-1,2,4-oxadiazolineHCID 178461247HCID 178461247, compound

Product 1

HCID 178461245HCID 178461245, compound

Procedure

Using a procedure analogous to that described in Example 3.94 (Step 3), and starting with 4-(5-chloropyridin-3-yl)-2-((2-fluorophenyl)amino)-N-hydroxy-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carboximidamide, 3-(4-(5-chloropyridin-3-yl)-2-(2-fluorophenyl)amino)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (TFA salt) was prepared. MS ESI calc'd. for C27H25ClFNγO2 [M+H]+ 534. found 534. 1H NMR (500 MHz, DMSO-d6) δ 12.83 (s, 1H), 9.27 (s, 1H), 8.83 (m, J=20.7, 2H), 8.39 (s, 1H), 7.81 (s, 1H), 7.65 (m, 1H), 7.26 (m, 3H), 3.85 (s, 2H), 1.44 (d, 2H), 1.07 (m, 2H), 0.71 (m, J=6.5, 7H), 0.54 (m, 2H)

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-baa026e9e10f417ea3d772417493e71a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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