Pyridine → HCID 67235313, compound

HRID 1748356Notes

Reaction equation

HRID 1748356 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.ClC(N(C)C)=C(C)C.[C:27]([O:36][CH3:37])(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH2:30].N1C=CC=CC=1>C(Cl)Cl.O>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[C:27]([O:36][CH3:37])=[O:35])=[O:18])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8635Methyl AnthranilateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Product 1

HCID 67235313HCID 67235313, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 500 mg, 2.0 mmol) in CH2Cl2 (10 mL) at room temperature is added 1-chloro-N,N,2-trimethylpropenylamine (0.98 mL, 7.2 mmol). After stirring for 3 h, methyl anthranilate (1.3 mL, 10.2 mmol) and pyridine (0.66 mL, 8.2 mmol) are added. The mixture is stirred for another 16 h at room temperature. Water (100 mL) is added and the mixture is extracted with EtOAc (3×100 mL). The organic layers are combined, dried and evaporated. Methanol (50 mL) is added to the oily residue, and a white solid is formed. The solid is filtered to afford the title compound (503 mg, 65%).

Workup

  1. stirringThe mixture is stirred for another 16 h at room temperature
  2. extractionthe mixture is extracted with EtOAc (3×100 mL)
  3. customdried
  4. customevaporated
  5. additionMethanol (50 mL) is added to the oily residue
  6. customa white solid is formed
  7. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-ce82ab99fc0d4d9da3b39e9075fabe82
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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