4-Acetamidophenylboronic acid → N-{4-[6-(4-Cyclopropyl-[1,4]diazepan-1-yl)pyridazin-3-yl]phenyl}acetamide, dihydrochloride

HRID 80922Notes

Reaction equation

HRID 80922 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([CH:15]3[CH2:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)(=[O:20])[CH3:19]>>[ClH:1].[ClH:1].[CH:15]1([N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:5]3[N:6]=[N:7][C:2]([C:25]4[CH:26]=[CH:27][C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:23][CH:24]=4)=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 27346574-Acetamidophenylboronic acidHCID 872861831-(6-Chloro-pyridazin-3-yl)-4-cyclopropyl-perhydro-1,4-diazepine

Product 1

HCID 131730780N-{4-[6-(4-Cyclopropyl-[1,4]diazepan-1-yl)pyridazin-3-yl]phenyl}acetamide, dihydrochloride

Procedure

The title compound was prepared by a similar procedure to that described in Example 68, starting from 1-(6-chloro-pyridazin-3-yl)-4-cyclopropyl-perhydro-1,4-diazepine and 4-acetamidophenylboronic acid. 1H NMR (400 MHz, CD3OD) δ 8.47 (d, 1H), 8.08 (d, 1H), 7.94 (d, 2H), 7.85 (d, 2H), 4.33 (broad m, 1H), 4.12 (broad m, 1H), 3.91 (broad m, 4H), 3.62 (broad m, 2H), 2.97 (hept, 1H), 2.55 ((broad m, 1H), 2.43 (broad m, 1H), 2.17 (s, 3H), 1.24 (broad m, 2H), 1.01 (d, 2H).

Sources & evidence

ORD record
ord-8a4d099e74044e5986736d68ebe9a625
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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