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

HRID 2361362Notes

Reaction equation

HRID 2361362 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3452b647ed244576bf1a89a5fdeed3eb
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…