5,6-Dichloro-3-oxoindan-1-carbonyl chloride → HCID 67705815, compound

HRID 1489516Notes

Reaction equation

HRID 1489516 reaction equation
[N:1]1([CH2:6][C@@H:7]2[CH2:12][S:11][CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:13]=[C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:24])=[C:20]([Cl:23])[CH:21]=2)[CH:16]([C:25](Cl)=[O:26])[CH2:15]1>C(N(CC)CC)C>[ClH:23].[N:1]1([CH2:6][C@@H:7]2[CH2:12][S:11][CH2:10][CH2:9][N:8]2[C:25]([C@@H:16]2[C:17]3[C:22](=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[C:14](=[O:13])[CH2:15]2)=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 151324075,6-Dichloro-3-oxoindan-1-carbonyl chlorideHCID 18645474HCID 18645474, compound

Product 1

HCID 67705815HCID 67705815, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A similar reaction to that of Example 1 was carried out by using 1.0 g of (3R)-3-(1-pyrrolidinyl)methylthiomorpholine, 2.0 ml of triethylamine and 3.0 g of 3-oxo-5,6-dichloro-1-indanecarboxylic acid chloride and the crude product was purified by column chromatography through silica gel using a 100:1 mixture of ethyl acetate and triethylamine as a mobile phase to give 0.82 g of the free basic form of the title compound from the less polar fractions. The product was treated with hydrogen chloride in a similar manner to the latter part of Example 1 to give 0.85 g of the title compound. m.p.: 257°-261° C. [α]D25 +26.8° (c=2.0, methanol)

Workup

  1. customA similar reaction to that of Example 1
  2. customthe crude product was purified by column chromatography through silica gel using
  3. additiona 100:1 mixture of ethyl acetate and triethylamine as a mobile phase

Sources & evidence

ORD record
ord-ffbdc0b1bd1f425e97b98a66d2d784f1
Source dataset
uspto-grants-1997_10
Patent number
US05679674

Reaction notes

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