Cyanoacetic acid hydrazide → HCID 178424707, compound

HRID 541262Notes

Reaction equation

HRID 541262 reaction equation
[CH3:1][C:2]1[CH:23]=[C:22]([CH3:24])[C:21]([C:25]2[NH:29][C:28]([CH2:30][CH:31]3CCOC3)=[N:27][N:26]=2)=[CH:20][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].C(CC(NN)=O)#[N:37].O1CCC(CC(NN)=O)C1>>[C:31]([CH2:30][C:28]1[NH:29][C:25]([C:21]2[C:22]([CH3:24])=[CH:23][C:2]([CH3:1])=[C:3]([CH:20]=2)[C:4]([N:6]2[CH2:7][CH2:8][CH:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:10][CH2:11]2)=[O:5])=[N:26][N:27]=1)#[N:37]

Participants

4

Reactant 3

HCID 8820Cyanoacetic acid hydrazide2×HCID 682888162-(Tetrahydrofuran-3-yl)acetohydrazideHCID 1784247044-(1-(2,4-dimethyl-5-(5-((tetrahydrofuran-3-yl)methyl)-4H-1,2,4-triazol-3-yl)benzoyl)piperidin-4-yl)benzonitrile2×

Product 1

HCID 178424707HCID 178424707, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of 4-(1-(2,4-dimethyl-5-(5-((tetrahydrofuran-3-yl)methyl)-4H-1,2,4-triazol-3-yl)benzoyl)piperidin-4-yl)benzonitrile (compound 130), using 2-cyanoacetohydrazide (compound 139.1) instead of 2-(tetrahydrofuran-3-yl)acetohydrazide (compound 130.4). m/z (ES+) 425 (M+H)+. 1H-NMR (300 Hz, CD3OD): δ 7.70 (d, J=8.4 Hz, 2H), 7.54-7.42 (m, 3H), 7.35 (s, 1H), 4.87-4.80 (m, 1H), 4.12 (s, 2H), 3.77-3.65 (m, 1H), 3.27-3.23 (m, 1H), 3.09-2.99 (m, 2H), 2.55 (s, 3H), 2.43 and 2.33 (2 singlets, amide rotamers, ArCH3, 3H), 2.05-2.00 (m, 1H), 1.83-1.76 (m, 3H).

Sources & evidence

ORD record
ord-35a134148af5424f9f012ac7c857f8cb
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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