2-Amino-6-fluorobenzonitrile → 3-(3-amino-2-cyanophenoxy)-N-cyclopentyl-2,2-dimethylpropanamide

HRID 1467018Notes

Reaction equation

HRID 1467018 reaction equation
[CH:1]1([NH:6][C:7](=[O:13])[C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18]>>[NH2:14][C:15]1[C:16]([C:17]#[N:18])=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:10][CH2:9][C:8]([CH3:11])([CH3:12])[C:7]([NH:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)=[O:13]

Participants

3

Reactant 2

HCID 5226592-Amino-6-fluorobenzonitrileHCID 66746460N-cyclopentyl-3-hydroxy-2,2-dimethylpropanamide

Product 1

HCID 667459063-(3-amino-2-cyanophenoxy)-N-cyclopentyl-2,2-dimethylpropanamide

Procedure

Prepared as in Example 22b from N-cyclopentyl-3-hydroxy-2,2-dimethylpropanamide (Example 29c) and 2-amino-6-fluorobenzonitrile as a white solid (45%). 1H NMR (400 MHz, DMSO-d6) δ 1.19 (s, 6H), 1.40-1.49 (m, 4H), 1.61-1.63 (m, 2H), 1.74-1.79 (m, 2H), 3.95 (s, 2H), 4.03 (m, 1H), 5.98 (s, 2H), 6.19 (d, J=8.0 Hz, 1H), 6.33 (d, J=8.0 Hz, 1H), 7.17 (t, J=8.0 Hz, 1H), 7.23 (d, J=8.0 Hz, 1H). MS 302 (MH+).

Sources & evidence

ORD record
ord-8fd13a49683940b384cca56536e7003d
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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