2-Amino-6-fluorobenzonitrile → 4-(3-amino-2-cyanophenoxy)-N-isopropylcyclohexanecarboxamide

HRID 2169903Notes

Reaction equation

HRID 2169903 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([NH:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]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:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([NH:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 5226592-Amino-6-fluorobenzonitrileHCID 667468294-hydroxy-N-isopropylcyclohexanecarboxamide

Product 1

HCID 667457454-(3-amino-2-cyanophenoxy)-N-isopropylcyclohexanecarboxamide

Procedure

Prepared as in Example 22b from 4-hydroxy-N-isopropylcyclohexanecarboxamide (Example 45c) and 2-amino-6-fluorobenzonitrile as an off-white solid (17%). 1H NR (400 MHz, DMSO-d6) δ 1.01 (d, J=6.4 Hz, 6H), 1.47-1.57 (m, 4H), 1.67-1.77 (m, 2H), 1.89-1.93 (m, 2H), 2.08-2.15 (m, 1H), 3.75-3.84 (m, 1H), 4.57 (brs, 1H), 5.93 (s, 2H), 6.19 (d, J=8.0 Hz, 1H), 6.28 (d, J=8.0 Hz, 1H), 7.13 (t, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H). MS 302 (MH+).

Sources & evidence

ORD record
ord-6261b67850e544a2bc1a6e859a71c6ca
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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