4-(Dimethylamino)-2-methoxybenzaldehyde → (1S,2S,3R,4R)-3-[2-(4-Dimethylamino-2-methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591976

反応式

HRID 591976 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[CH:5]=[CH:4][N:3]=1.[CH3:20][N:21]([CH3:32])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[C:24]([O:30][CH3:31])[CH:23]=1>>[CH3:32][N:21]([CH3:20])[C:22]1[CH:29]=[CH:28][C:25]([C:26]2[NH:1][C:2]3=[N:3][CH:4]=[CH:5][C:6]([NH:9][C@@H:10]4[C@@H:15]5[CH2:16][C@@H:12]([CH:13]=[CH:14]5)[C@@H:11]4[C:17]([NH2:19])=[O:18])=[C:7]3[N:8]=2)=[C:24]([O:30][CH3:31])[CH:23]=1

参加物

3

反応物 2

HCID 2913504-(Dimethylamino)-2-methoxybenzaldehydeHCID 117701640HCID 117701640、化合物

生成物 1

HCID 178493179(1S,2S,3R,4R)-3-[2-(4-Dimethylamino-2-methoxy-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide収率 29%

実験手順

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.0 mg, 0.193 mmol) and 4-dimethylamino-2-methoxy-benzaldehyde (38.0 mg, 0.212 mmol) were reacted to produce 20 mg (29%) of the title compound. mp: 185-190° C., 1H NMR (300 MHz, DMSO-d6): 11.78 (s, 1H), 8.00 (d, J=8 Hz, 1H), 7.85 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.14 (s, 1H), 6.69 (d, J=8 Hz, 2H), 6.46 (d, J=8 Hz, 1H), 6.36 (d, J=8 Hz, 1H), 6.32 (br s, 3H), 3.96 (s, 3H), 3.01 (s, 6H), 2.86 (s, 1H), 2.75 (s, 1H), 2.59 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 1.42 (d, J=8 Hz, 1H). MS: 419 (M+H), HPLC: 2.09 min (G method).

出典と根拠

ORDレコード
ord-5205ea89a67841a8a65b4ef9e7ebc55f
出典データセット
uspto-grants-2016_01
特許番号
US09238656B2

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