4-Methylmorpholine → benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate

HRID 2361405ノート

反応式

HRID 2361405 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:36])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([Br:31])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:32](O)=[O:33])=[N:20][C:19]=2[CH3:35])[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.[N:46]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Br:31][C:26]1[CH:25]=[C:24]2[C:29]([C:30]3[C:18]([C:14]4[C:13]([CH3:36])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH:17]=[CH:16][CH:15]=4)=[C:19]([CH3:35])[N:20]=[C:21]([C:32](=[O:33])[NH2:46])[C:22]=3[NH:23]2)=[CH:28][CH:27]=1

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679947674-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid

生成物 1

HCID 70651685benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(3-(((benzyloxy)carbonyl)amino)-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid (1.10 g, 2.02 mmol), ammonium chloride (0.432 g, 8.08 mmol), BOP (1.16 g, 2.63 mmol), N-methylmorpholine (0.866 mL, 7.88 mmol), and diisopropylethylamine (1.69 mL, 9.70 mmol) in N,N-dimethylformamide (10.0 mL) was stirred at room temperature for 4 h. The reaction mixture was added dropwise to rapidly stirring water (100 mL). After stirring for 60 min., the suspension was filtered under reduced pressure, and the solid was washed with water and dried well under reduced pressure to give benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate as a light brown solid. LC/MS M+1=543.4 and 545.4. The reaction mixture was used in the next step without any further purification.

後処理

  1. stirringAfter stirring for 60 min.
  2. filtrationthe suspension was filtered under reduced pressure
  3. washthe solid was washed with water
  4. customdried well under reduced pressure

出典と根拠

ORDレコード
ord-51a9402543864aeeb6acb3945b12aafe
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

読み込み中…