1-Hydroxybenzotriazole → {(S)-3-Phenyl-2-[(2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 222112ノート

反応式

HRID 222112 の反応式
[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[C:8]=2[C:20](O)=[O:21])[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:32]([O:36][C:37](=[O:49])[NH:38][CH2:39][C@@H:40]([NH2:48])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:35])([CH3:34])[CH3:33].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:32]([O:36][C:37](=[O:49])[NH:38][CH2:39][C@@H:40]([NH:48][C:20]([C:8]1[C:9]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[NH:19][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:21])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([CH3:35])([CH3:33])[CH3:34]

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53637716(S)-tert-Butyl (2-amino-3-phenylpropyl)carbamateHCID 687095872-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid

生成物 1

HCID 68707419{(S)-3-Phenyl-2-[(2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid G2 (0.087 mmol) in DMF (1 mL), DIEA (0.26 mmol) and ((S)-2-amino-3-phenyl-propyl) -carbamic acid tert-butyl ester (0.13 mmol) were added. The mixture was cooled to 0° C., EDCI hydrochloride (0.13 mmol) and HOBT (0.13 mmol) were added and stirring was kept overnight at rt. The suspension was filtered and the solid was washed with aq saturated NaHCO3 and with water. After drying, the title compound was isolated in 43% yield. ESI (+) MS: m/z 521 (MH+). 1H NMR: 1.40 (s, 9H) 2.80-2.89 (m, 1H) 3.00-3.11 (m, 2H) 3.12-3.21 (m, 1H) 4.18-4.30 (m, 1H) 6.91-6.97 (m, 1H) 7.00-7.06 (m, 1H) 7.16-7.23 (m, 1H) 7.25-7.34 (m, 4H) 7.37-7.43 (m, 1H) 7.49-7.56 (m, 2H) 7.88 (d, J=7.62, 2H) 8.00 (d, J=9.00, 1H) 8.31 (d, J=9.00, 1H) 8.72 (s, 2H) 9.51 (s, 1H) 11.72 (bs, 1H).

後処理

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with aq saturated NaHCO3 and with water
  3. customAfter drying

出典と根拠

ORDレコード
ord-ee6d9b0668c54683bc481363076f0244
出典データセット
uspto-grants-2012_06
特許番号
US08207180B2

反応ノート

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