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

HRID 1887158Notes

Reaction equation

HRID 1887158 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-af6ada44c0f541a4b4c1da520b251c26
Source dataset
uspto-grants-2013_08
Patent number
US08501739B2

Reaction notes

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