4-Morpholinobenzaldehyde → (1S,2S,3R,4R)-3-[6-Bromo-2-(4-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591964

反応式

HRID 591964 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])[C:5]([Br:20])=[CH:4][N:3]=1.[N:21]1([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[Br:20][C:5]1[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])=[C:7]2[N:8]=[C:31]([C:30]3[CH:29]=[CH:28][C:27]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:34][CH:33]=3)[NH:1][C:2]2=[N:3][CH:4]=1

参加物

3

反応物 2

HCID 2913494-MorpholinobenzaldehydeHCID 117701905(1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

生成物 1

HCID 178513975(1S,2S,3R,4R)-3-[6-Bromo-2-(4-morpholin-4-yl-phenyl)-3H-imidazo[4,5-b]pyridin-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide収率 75%

実験手順

In a similar fashion to Compound LXXVI, (1S,2S,3R,4R)-3-(2,3-Diamino-5-bromo-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (40.0 mg, 0.118 mmol) and 4-morpholin-4-yl-benzaldehyde (24.9 mg, 0.130 mmol) were reacted to produce 45 mg (75%) of the title compound. mp: 283-284° C., 1H NMR (300 MHz, DMSO-d6): 12.97 (s, 1H), 8.22 (s, 1H), 8.00 (d, J=8 Hz, 2H), 7.93 (s, 1H), 7.65 (s, 1H), 7.11 (s, 1H), 7.03 (d, J=8 Hz, 2H), 6.98 (d, J=8 Hz, 1H), 6.36 (br s, 1H), 6.33 (br s, 1H), 5.27 (t, J=8 Hz, 1H), 3.77 (br s, 4H), 2.88 (s, 1H), 2.77 (s, 1H), 2.62 (d, J=7 Hz, 1H), 2.26 (br s, 4H), 1.39 (d, J=8 Hz, 1H). MS: 509, 511 (M+H), HPLC: 2.31 min (G method).

出典と根拠

ORDレコード
ord-1ecbf132aec048dfa46e35a961b455d5
出典データセット
uspto-grants-2016_01
特許番号
US09238656B2

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