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

HRID 1409463Notes

Reaction equation

HRID 1409463 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][C@@H:16]([CH3:33])[CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[C:29]([F:31])[C:26]([C:27]#[N:28])=[C:25]([Cl:32])[CH:24]=2)=[N:19]1>>[Cl:32][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][C@@H: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])[CH3:33])[N:19]=2)[CH:30]=[C:29]([F:31])[C:26]=1[C:27]#[N:28]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70981191Ethyl 3-(2-hydroxypropan-2-yl)-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 86714672(S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-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 (2 mmol, 400 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (2 mmol, 556 mg). Yield 202 mg. 1H-NMR (400 MHz; DMSO-d6): δ 1.12 (d, 3H), 1.51 (bs, 6H), 4.34-4.37 (m, 2H), 4.43-4.51 (m, 1H), 5.70 (s, 1H), 7.02 (d, 1H), 7.83-7.88 (m, 2H), 7.96 (s, 1H), 9.41 (d, 1H). LC-MS: [M+1]=433.20.

Sources & evidence

ORD record
ord-02e3b1a64b8448d899038273507b3824
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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