5-Bromosalicylic acid → HCID 11744211, compound

HRID 2384313Notes

Reaction equation

HRID 2384313 reaction equation
CCN=C=NCCCN(C)C.Cl.[Br:13][C:14]1[CH:22]=[C:18]([C:19]([OH:21])=O)[C:17]([OH:23])=[CH:16][CH:15]=1.[NH2:24][CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:34]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[O:35])[CH:31]=2)[CH2:26]1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([OH:23])=[C:18]([CH:22]=1)[C:19]([NH:24][CH:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:34]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[O:35])[CH:31]=2)[CH2:26]1)=[O:21]

Participants

7

Reactant 4

HCID 69725-Bromosalicylic acidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23069946HCID 23069946, compound

Product 1

HCID 11744211HCID 11744211, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

WSC.HCl (96 mg, 0.5 mmol) was added to a solution of 5-bromosalicylic acid (109 mg, 0.5 mmol), 2-amino-5-(morpholino)carbonylindan (refer to Chem. Pharm. Bull., 2000, 48, 131; 141 mg, 0.5 mmol) and triethylamine (70 μL, 0.5 mmol) in dichloromethane (5 mL), and the mixture was stirred at 40° C. for 1.5 hours. After cooling, the reaction mixture was diluted with ethyl acetate, washed with 2 N hydrochloric acid, water and brine one after another, dried over anhydrous magnesium sulfate, concentrated, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1) to give the title compound (26 mg, 11.9%) as a white crystal.

Workup

  1. temperatureAfter cooling
  2. washwashed with 2 N hydrochloric acid, water and brine one after another,
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1)

Sources & evidence

ORD record
ord-75d703797cde45118195ae29acb87240
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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