4-Methylmorpholine → Benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

HRID 2361362ノート

反応式

HRID 2361362 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:35])=[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]([OH:34])=O)=[N:20][CH:19]=2)[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+].C([N:41](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.O>[Br:31][C:26]1[CH:25]=[C:24]2[C:29]([C:30]3[C:18]([C:14]4[C:13]([CH3:35])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:17]=[CH:16][CH:15]=4)=[CH:19][N:20]=[C:21]([C:32](=[O:34])[NH2:41])[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 679946604-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxylic acid

生成物 1

HCID 67994872Benzyl 3-(7-bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxylic acid (1.174 g, 2.214 mmol), ammonium chloride (0.474 g, 8.85 mmol), N,N-diisopropylethylamine (1.856 mL, 10.63 mmol), BOP (1.273 g, 2.88 mmol), and N-methylmorpholine (0.949 mL, 8.63 mmol) in DMF (Volume: 10 mL) was stirred at room temperature for 2 hr. To the mixture was added water (120 mL), and the resulting mixture was stirred at room temperature for 20 min. The precipitating product (1.23 g) was collected as a beige solid by suction filtration and dried over Drierite at 50° C. This product was 80% pure, but was used in the next step without further purification.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 20 min
  2. filtrationThe precipitating product (1.23 g) was collected as a beige solid by suction filtration
  3. dry with materialdried over Drierite at 50° C
  4. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-3452b647ed244576bf1a89a5fdeed3eb
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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