860371-76-2 → HCID 67173614, compound

HRID 872927Notes

Reaction equation

HRID 872927 reaction equation
[NH2:1][C@@H:2]([CH3:19])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[C:15]([F:17])[C:12]([C:13]#[N:14])=[C:11]([Cl:18])[CH:10]=2)=[N:5]1.[OH:20][C:21]([C:24]1[O:28][N:27]=[C:26]([C:29](O)=[O:30])[CH:25]=1)([CH3:23])[CH3:22]>>[Cl:18][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@@H:2]([NH:1][C:29]([C:26]3[CH:25]=[C:24]([C:21]([OH:20])([CH3:22])[CH3:23])[O:28][N:27]=3)=[O:30])[CH3:19])[N:5]=2)[CH:16]=[C:15]([F:17])[C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 67168640860371-76-2HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 67173614HCID 67173614, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (120 mg, 0.431 mmol) and 5-(2-hydroxypropan-2-yl)isoxazole-3-carboxylic acid (96 mg, 0.560 mmol). The product was triturated with ethanol. Yield 67 mg (36%). 1H-NMR (400 MHz; d6-DMSO): δ 1.17 (d, 3H), 1.47 (s, 6H), 4.31-4.33 (m, 2H), 4.40-4.49 (m, 1H), 6.49 (s, 1H), 7.01 (d, 1H), 7.84 (d, 1H), 7.85-7.88 (m, 1H), 7.99 (s, 1H), 8.74 (d, 1H).

Workup

  1. customThe product was triturated with ethanol

Sources & evidence

ORD record
ord-37bafc5390f844669ecb32d71022b25f
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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