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

HRID 2361405Notes

Reaction equation

HRID 2361405 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-51a9402543864aeeb6acb3945b12aafe
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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