tert-butyl N-(2-hydroxyethyl)carbamate → 4-(1-(2-Aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

HRID 872475Notes

Reaction equation

HRID 872475 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([C:11]2[NH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].O[CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C>>[NH2:19][CH2:18][CH2:17][N:14]1[CH:13]=[CH:12][C:11]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([Cl:2])[CH:10]=2)=[N:15]1

Participants

3

Reactant 2

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 671717272-Chloro-4-(1H-pyrazol-3-yl)benzonitrile hydrochloride

Product 1

HCID 671701664-(1-(2-Aminoethyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Procedure

The title compound was prepared using the method of Example 34(c) starting from 2.3 g of 2-chloro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride, 1.7 ml dipea and 1.7 g tert-butyl 2-hydroxyethylcarbamate yielding 2.08 g of the product. 1H-NMR (400 MHz; d6-DMSO): δ 1.56 (s, 2H), 2.97 (t, 2H), 4.13-4.17 (t, 2H), 6.97 (s, 1H), 7.87 (d, 1H), 7.93-8.02 (m, 2H), 8.10 (d, 1H).

Sources & evidence

ORD record
ord-e484011cf17f4f479956b237353578e3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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