tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate → (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

HRID 872737Notes

Reaction equation

HRID 872737 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH:7]=[C:6]([F:15])[C:3]=1[C:4]#[N:5].O[CH2:17][C@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19]>>[NH2:20][C@H:18]([CH3:19])[CH2:17][N:12]1[CH:13]=[CH:14][C:10]([C:8]2[CH:7]=[C:6]([F:15])[C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[N:11]1

Participants

3

Reactant 2

HCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamateHCID 178510273HCID 178510273, compound

Product 1

HCID 70656221(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileYield 70.5%

Procedure

(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile was prepared using the method of Example 202 starting from 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile (5.0 g, 22.56 mmol) and (R)-tert-butyl (1-hydroxypropan-2-yl)carbamate (7.91 g, 45.1 mmol). The product was evaporated to dryness. Yield 70.5%. 1H-NMR (400 MHz; DMSO): δ 0.96 (d, 3H), 3.20-3.30 (m, 1H), 4.00-4.10 (m, 2H), 7.03 (d, 1H), 7.85-7.91 (m, 2H), 7.99 (m, 1H).

Workup

  1. customThe product was evaporated to dryness

Sources & evidence

ORD record
ord-cefa2d0c97eb4907a9d0cd5d14bc2b1c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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