N-Boc-(R)-1-amino-2-propanol → (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

HRID 1409445Notes

Reaction equation

HRID 1409445 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[C@H:17]([CH3:27])[CH2:18][NH:19]C(=O)OC(C)(C)C>>[NH2:19][CH2:18][C@@H: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)[CH3:27]

Participants

3

Reactant 2

HCID 12094522N-Boc-(R)-1-amino-2-propanolHCID 178510273HCID 178510273, compound

Product 1

HCID 67171415(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Procedure

The title compound was prepared using the procedure described in Example 3(g) starting from 2-chloro-6-fluoro-4-(1H-pyrazol-3-yl)benzonitrile (13.5 mmol, 3 g) and (R)-tert-butyl (2-hydroxypropyl)carbamate (27 mmol, 4.72 g). Yield 1.3 g. 1H-NMR (400 MHz; CDCl3): δ 1.47 (d, 3H), 3.02-3.19 (m, 2H), 4.30-4.38 (m, 1H), 6.60 (d, 1H), 7.52-7.59 (m, 2H), 7.75 (s, 1H). LC-MS: [M+1]=279.17.

Sources & evidence

ORD record
ord-ece6608a7139477aa9b84c3e47bc85bc
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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