HCID 22319317, compound → HCID 10161478, compound

HRID 497441Notes

Reaction equation

HRID 497441 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:16][C:17]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:18]=3[C:19]([O:21]C)=[O:20])[CH:13]=2)[CH2:8]1>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:5][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:16][C:17]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:18]=3[C:19]([OH:21])=[O:20])[CH:13]=2)[CH2:8]1

Participants

3

Reactant 1

HCID 22319317HCID 22319317, compound

Product 1

HCID 10161478HCID 10161478, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The methyl benzoate (0.130 g) was taken up in 20 mL 1:1 THF/MeOH and was treated with 1 M LIOH (3 mL). The mixture was stirred at room temperature for 48 hours. The mixture was then concentrated, and the residual oil was purified by chromatography (MPLC, silica, gradient 95:5 to 75:25 (CH2Cl2/MeOH). Fractions containing the desired product were combined, concentrated, and dried in vacuo overnight to give 2-[2-(3,4-dichlorobenzylamino)-indan-5-ylamino]-5-methoxy-benzoic acid (0.03 g, 24% yield). MS (APCI) m/z 457.0 (M++1). CHN for (C24H22Cl2N2O3·0.6H2O) calc: C, 61.57, H, 4.98, N, 5.98; found: C, 61.23, H, 4.88, N, 5.69.

Workup

  1. additionwas treated with 1 M LIOH (3 mL)
  2. concentrationThe mixture was then concentrated
  3. customthe residual oil was purified by chromatography (MPLC, silica, gradient 95:5 to 75:25 (CH2Cl2/MeOH)
  4. additionFractions containing the desired product
  5. concentrationconcentrated
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-5147982dad214a348d93f07437121180
Source dataset
uspto-grants-2005_09
Patent number
US06949575B2

Reaction notes

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