Water → HCID 68517179, compound

HRID 1916294Notes

Reaction equation

HRID 1916294 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:17](Cl)=[N:16][CH:15]=[N:14][C:10]=3[NH:11]2)=[CH:7][CH:6]=1)=[O:4].N1CCO[CH:21]([N:25](C)[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])C1.C([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])C.[OH2:41]>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:17]([N:36]4[CH2:37][CH2:38][O:41][CH:40]([CH2:21][NH:25][C:26]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:32])[CH2:39]4)=[N:16][CH:15]=[N:14][C:10]=3[NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 53346552HCID 53346552, compoundHCID 59447943HCID 59447943, compound

Product 1

HCID 68517179HCID 68517179, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylic acid methyl ester (231 mg, 0.88 mmol), tert-butyl morpholin-2-yl-methylcarbamate (382 mg, 1.77 mmol), and triethylamine (246 μL, 1.77 mmol) in NMP was irradiated in a microwave at 140° C. for 15 minutes. An additional 246 μL of triethylamine was added to the reaction mixture and the irradiation repeated. The reaction mixture was then added to 5 mL water and the resulting precipitate was collected by filtration and purified by flash chromatography to give the title compound (39 mg, 0.088 mmol). LC-MS (2) Rt 2.67 min; m/z (ES+) 442.

Workup

  1. customwas irradiated in a microwave at 140° C. for 15 minutes
  2. customthe irradiation
  3. filtrationthe resulting precipitate was collected by filtration
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a8f65dba11584077b93e614bb0d3b5ad
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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