Stannous chloride dihydrate → 3-isopropyl-1-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-5-amine

HRID 1711692ノート

反応式

HRID 1711692 の反応式
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[CH:3]1.[N:12]([O-])=O.[Na+].O.O.Cl[Sn]Cl.[CH3:21][CH:22]([CH3:28])[C:23](=O)[CH2:24][C:25]#[N:26]>>[CH:22]([C:23]1[CH:24]=[C:25]([NH2:26])[N:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[CH:3]=[N:4][C:5]=3[CH:10]=2)[N:12]=1)([CH3:28])[CH3:21]

参加物

5

反応物 4

HCID 61436Stannous chloride dihydrateHCID 3154991-methyl-1H-1,3-benzodiazol-5-amineHCID 101299214-Methyl-3-oxopentanenitrileHCID 23668193Sodium Nitrite

生成物 1

HCID 672540493-isopropyl-1-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-5-amine収率 73%

実験手順

Using a procedure analogous to Example B22, 1-methyl-1H-benzo[d]imidazol-5-amine (0.50 g, 3.4 mmol), NaNO2 (0.28 g, 4.1 mmol), SnCl2.2H2O (2.8 g, 14 mmol) and 4-methyl-3-oxopentanenitrile (0.45 g, 4.1 mmol) were combined to afford crude 3-isopropyl-1-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-5-amine (0.63 g, 73% yield) as a foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (s, 1H), 7.72 (dd, J=0.40 and 1.2 Hz, 1H), 7.60 (dd, J=0.40 and 8.4 Hz, 1H), 7.42 (dd, J=2.0 and 8.4 Hz, 1H), 5.32 (s, 1H), 5.08 (brs, 2H), 3.85 (s, 3H), 2.75 (septet, J=6.8 Hz, 1H), 1.16 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 250.0 (M+H+).

出典と根拠

ORDレコード
ord-32c6a3761572456db103eaff501334a2
出典データセット
uspto-grants-2010_09
特許番号
US07790756B2

反応ノート

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