Acetic Acid → (E)-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-N-(1-benzyl-pyrrolidin-3-yl)-3-phenyl-acrylamide

HRID 2250875

反応式

HRID 2250875 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[C:23](=[O:25])[CH3:24])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCC(=O)C1)C1C=CC=CC=1.C(N1C2C(=CC=C(N)C=2)CC1)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.[C:70](Cl)(=[O:79])[CH:71]=[CH:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>ClCCCl>[C:23]([N:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]([N:13]([CH:10]3[CH2:11][CH2:12][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9]3)[C:70](=[O:79])/[CH:71]=[CH:72]/[C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[CH:22]=2)[CH2:18][CH2:19]1)(=[O:25])[CH3:24]

参加物

8

反応物 6

HCID 176Acetic AcidHCID 660233-Phenylprop-2-enoyl chlorideHCID 698901-Benzyl-3-pyrrolidinoneHCID 2585641-Acetyl-6-aminoindolineHCID 5049666Sodium triacetoxyborohydrideHCID 692108041-[6-(1-Benzyl-pyrrolidin-3-ylamino)-2,3-dihydro-indol-1-yl]-ethanone

生成物 1

HCID 11294247(E)-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-N-(1-benzyl-pyrrolidin-3-yl)-3-phenyl-acrylamide収率 74%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

1-[6-(1-benzyl-pyrrolidin-3-ylamino)-2,3-dihydro-indol-1-yl]-ethanone. The desired intermediate (84 mg, 44%) was prepared as in Example 39, Step A, using 1-benzyl-3-pyrrolidinone (0.20 g, 1.1 mmol), 1-acetyl-6-aminoindoline (0.10 g, 0.57 mmol), Na(OAc)3BH (360 mg, 1.7 mmol), and AcOH (171 μL, 3.0 mmol) in 1,2-dichloroethane (10 mL). 1H NMR (500 MHz, CDCl3): 7.61 (s, 1H), 7.35-7.28 (m, 4H), 7.28-7.20 (m, 1H), 6.93 (d, J=8.1 Hz,1H), 6.24 (dd, J=8.2, 1.9 Hz, 1H), 4.05-3.96 (m, 3H), 3.68-3.56 (m, 2H), 3.10-3.01 (m, 2H), 2.80-2.71 (m, 2H), 2.59-2.51 (m, 1H), 2.48-2.39 (m, 1H), 2.38-2.22 (m, 1H), 2.20 (s, 3H), 1.71-1.56 (m, 1H). MS: exact mass calculated for C21H25N3O, 335.20; m/z found, 336.1 [M+H]+. Step B. The above intermediate (49 mg, 0.29 mmol) was reacted with with cinnamoyl chloride (2 76 mg, 0.2 mmol) as in Example 2, Step C to provide 79 mg (74%) of the desired product. 1H NMR (500 MHz, CDCl3): 8.09 (s, 1H), 7.62 (d, J=15.5 Hz, 1H), 7.30-7.15 (m, 1H), 6.78 (d, J=7.0 Hz, 1H), 6.17 (d, J=15.5 Hz, 1H), 5.15-5.05 (br m, 1H), 4.19-4.08 (m, 2H), 3.70-3.51 (m, 2H), 3.29-3.20 (m, 2H), 3.07-2.95 (br m, 1H), 2.76-2.57 (br m, 3H), 2.30-2.22 (m, 1H), 2.21 (s, 3H), 1.98-1.83 (m, 1H). MS: exact mass calculated for C30H31N3O2, 465.24; m/z found, 466.2 [M+H]+.

出典と根拠

ORDレコード
ord-2ed22e8ffb7e4faeb533de7542d22656
出典データセット
uspto-grants-2008_01
特許番号
US07317025B2

関連ノート

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