Dichloromethane → (4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

HRID 731304Notes

Reaction equation

HRID 731304 reaction equation
C(O[C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:5])C.[I:20][C:21]1[CH:36]=[CH:35][C:24]2[NH:25][C:26]([CH2:31][C:32](O)=[O:33])=[N:27][S:28](=[O:30])(=[O:29])[C:23]=2[CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1.ClCCl>CN(C)C=O.C(OCC)(=O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:11]2[C@@H:7]3[C@@H:6]([CH2:10][CH2:9][CH2:8]3)[C:4]([OH:5])=[C:31]([C:26]3[NH:25][C:24]4[CH:35]=[CH:36][C:21]([I:20])=[CH:22][C:23]=4[S:28](=[O:29])(=[O:30])[N:27]=3)[C:32]2=[O:33])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 25231427HCID 25231427, compoundHCID 59853574(7-Iodo-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

Product 1

HCID 135955738(4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of cis-2-(4-fluoro-benzylamino)-cyclopentanecarboxylic acid ethyl ester (prepared as described in Example 11, 1.33 g, 5 mmol) and (7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (2.20 g, 6.0 mmol) in anhydrous N,N-dimethylformamide (15 mL) under a nitrogen atmosphere, a 1.0 M solution of N,N′-dicyclohexylcarbodiimide solution in dichloromethane (6.5 mL, 6.5 mmol) was slowly added. After stirring for 1.5 h at 25° C., the mixture was diluted with ethyl acetate, washed with water and saturated aqueous brine solution, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to afford the amide intermediate, which was used directly in the next step without further purification.

Workup

  1. washwashed with water and saturated aqueous brine solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3664809029f24c779601327ad3181c95
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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