Ethylenediamine → HCID 118093786, compound

HRID 1056999Notes

Reaction equation

HRID 1056999 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[C:22]3[NH:21][C:20](=[O:23])[N:19]([CH3:24])[C:18]=3[CH:17]=[CH:16][C:15]=2[C:25]2[C:26]3[CH:35]=[CH:34][N:33](COCC[Si](C)(C)C)[C:27]=3[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=2)=[CH:11][CH:10]=1.C(N)CN>C(Cl)Cl.CO>[Cl:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[C:22]3[NH:21][C:20](=[O:23])[N:19]([CH3:24])[C:18]=3[CH:17]=[CH:16][C:15]=2[C:25]2[C:26]3[CH:35]=[CH:34][NH:33][C:27]=3[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 123485499HCID 123485499, compound

Product 1

HCID 118093786HCID 118093786, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.50 mL) was added dropwise to a solution of 4-(4-chlorophenoxy)-1-methyl-5-(6-methyl-7-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one (0.057 g, 0.103 mmol) in methylene chloride (0.50 mL), and the resultant reaction mixture was stirred at RT for 3 h, after which time the reaction mixture was concentrated in vacuo to give a residue. This residue was dissolved in methanol (0.50 mL), treated with ethylenediamine (0.131 mL, 1.95 mmol) dropwise, and the resultant solution was stirred at RT for 16 h. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (24.6 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 11.96 (br s, 1H), 11.20 (br s, 1H), 7.23 (dd, J=2.7, 2.7 Hz, 1H), 7.21-6.99 (m, 5H), 6.70-6.48 (m, 2H), 6.25-6.06 (m, 1H), 3.43 (s, 3H), 3.33 (s, 3H); LCMS calculated for C22H18ClN4O3 (M+H)+: m/z=421.1. found: 421.1.

Workup

  1. customthe resultant reaction mixture
  2. concentrationafter which time the reaction mixture was concentrated in vacuo
  3. customto give a residue
  4. customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-d7d69e19d0f54fa3bbdcd09ef67b84a1
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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