(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → (S)-N-(2-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propyl)-3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazole-5-carboxamide

HRID 1409462Notes

Reaction equation

HRID 1409462 reaction equation
[OH:1][C:2]([C:5]1[N:9]=[C:8]([C:10]([O:12]CC)=O)[O:7][N:6]=1)([CH3:4])[CH3:3].[NH2:15][CH2:16][C@@H:17]([N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[C:30]([F:32])[C:27]([C:28]#[N:29])=[C:26]([Cl:33])[CH:25]=2)=[N:20]1)[CH3:18]>>[Cl:33][C:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][N:19]([C@@H:17]([CH3:18])[CH2:16][NH:15][C:10]([C:8]3[O:7][N:6]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[N:9]=3)=[O:12])[N:20]=2)[CH:31]=[C:30]([F:32])[C:27]=1[C:28]#[N:29]

Participants

3

Reactant 2

HCID 67171415(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70981191Ethyl 3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 70981038(S)-N-(2-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propyl)-3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazole-5-carboxamide

Procedure

The title compound was prepared using the procedure described in Example 52(g) starting from ethyl 3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazole-5-carboxylate (1.5 mmol, 300 mg) and (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.5 mmol, 417 mg). Yield 160 mg. 1H-NMR (400 MHz; DMSO-d6): δ 1.49 (bs, 9H), 3.57-3.64 (m, 1H), 3.68-3.76 (m, 1H), 4.69-4.75 (m, 1H), 5.69 (s, 1H), 7.02 (d, 1H), 7.89 (d, 1H), 7.94 (d, 1H), 7.99 (s, 1H), 9.46 (t, 1H). LC-MS: [M+1]=433.17.

Sources & evidence

ORD record
ord-af9cb03ef634437cb33d20acf8ec81fe
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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