(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714682, compound

HRID 1409477Notes

Reaction equation

HRID 1409477 reaction equation
[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][C:4]1[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:7]=[C:6]([C:17]([OH:19])=O)[CH:5]=1.[NH2:22][C@@H:23]([CH3:40])[CH2:24][N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:37]=[C:36]([F:38])[C:33]([C:34]#[N:35])=[C:32]([Cl:39])[CH:31]=2)=[N:26]1>>[Cl:39][C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][N:25]([CH2:24][C@@H:23]([NH:22][C:17]([C:6]3[CH:5]=[C:4]([CH2:3][C:2]([OH:1])([CH3:21])[CH3:20])[N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[N:7]=3)=[O:19])[CH3:40])[N:26]=2)[CH:37]=[C:36]([F:38])[C:33]=1[C:34]#[N:35]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70981028HCID 70981028, compound

Product 1

HCID 86714682HCID 86714682, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 5-(2-hydroxy-2-methylpropyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrazole-3-carboxylic acid (1.59 mmol, 500 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.59 mmol, 442 mg). The product was purified by flash-chromatography. Yield 295 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.13 (s, 9H), 0.68 (t, 2H), 1.06 (s, 3H), 1.08 (s, 3H), 1.20 (d, 3H), 2.61 (s, 2H), 3.40 (t, 2H), 4.23-4.42 (m, 3H), 4.51 (s, 1H), 5.54 (d, 1H), 5.68 (d, 1H), 6.72 (s, 1H), 7.01 (d, 1H), 7.84-7.87 (m, 2H), 7.96 (s, 1H), 8.40 (d, 1H). LC-MS: [M+1]=575.01.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-e01b2a19eb2845a88c7571c17a222e2b
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…