1-Cyclopropylethanamine → 4-(Aminocarbonyl)-2-chloro-3-[(1-cyclopropylethyl)amino]benzoic acid

HRID 906176Notes

Reaction equation

HRID 906176 reaction equation
Br[C:2]1[C:3]([Cl:15])=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[N:14])[C:5]([O:7]CC)=[O:6].BrC1C(C#N)=CC(Cl)=C(C=1)C(OCC)=[O:23].[CH:31]1([CH:34]([NH2:36])[CH3:35])[CH2:33][CH2:32]1>>[NH2:14][C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([OH:7])=[O:6])=[C:3]([Cl:15])[C:2]=1[NH:36][CH:34]([CH:31]1[CH2:33][CH2:32]1)[CH3:35])=[O:23]

Participants

4

Reactant 3

HCID 5192391-CyclopropylethanamineHCID 67402907HCID 67402907, compoundHCID 67403496HCID 67403496, compound

Product 1

HCID 577486354-(Aminocarbonyl)-2-chloro-3-[(1-cyclopropylethyl)amino]benzoic acid

Procedure

Synthesized according to the method of reagent preparation 46 by first conducting step 2 to give a mixture of ethyl 3-bromo-2-chloro-4-cyanobenzoate and ethyl 5-bromo-2-chloro-4-cyanobenzoate then proceeding with step 1 using 1-cyclopropylethylamine followed by steps 3 and 4. 1HNMR (400 MHz, CD3OD): 7.49 (d, 1H), 7.22 (d, 1H), 2.84 (q, 2H), 1.17 (d, 3H), 0.9-0.76 (m, 1H), 0.3-0.26 (m, 2H), 0.04-0.00 (m, 2H). MS (EI) for C13H15ClN2O3: 284 (MH+).

Workup

  1. customSynthesized
  2. customaccording to the method of reagent preparation 46
  3. customto give

Sources & evidence

ORD record
ord-9c4f7157d1274f7a85e639698c2b0733
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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