4-Chloro-2-pyridinecarbonitrile → HCID 68816753, compound

HRID 734359Notes

Reaction equation

HRID 734359 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[Cl:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[N:28])[CH:22]=1>>[ClH:20].[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:15][CH2:16][N:17]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[N:28])[CH:22]=4)[CH2:18][CH2:19]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6933424-Chloro-2-pyridinecarbonitrileHCID 53420780(4-Cyclobutyl-1,4-diazepan-1-yl)(piperidin-4-yl)methanone

Product 1

HCID 68816753HCID 68816753, compound

Procedure

The title compound (E137) was prepared in a similar manner to that described in Example 98, using 1-cyclobutyl-4-(piperidine-4-carbonyl)-[1,4]-diazepane (D10) and 4-chloro-2-cyanopyridine (T. Sakamoto, S-I. Kaneda, S. Nishimura and H. Yamanaka, Chem. Pharm. Bull., 1985, 33(2), 565-571). 1H NMR δ [DMSO-d6]: 1.51-1.83 (6H, m), 2.01-2.23 (3H, m), 2.37-2.49 (3H, m), 2.72-3.15 (5H, m), 3.30-3.85 (6H, m), 4.01-4.10 (3H, m), 7.14 (1H, dd, J=7, 3 Hz), 7.64 (1H, d, J=3 Hz), 8.26 (1H, d, J=7 Hz), 11.19 and 11.34 (2×br. m, in ˜2:1 ratio, total of 1H); LCMS electrospray (+ve) 368 (MH+).

Sources & evidence

ORD record
ord-8c5321174f914a5fad334f49350e1c47
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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