Dicyclohexylcarbodiimide → HCID 57671245, compound

HRID 731244Notes

Reaction equation

HRID 731244 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:21]=[CH:20][C:9]2[NH:10][C:11]([CH2:16][C:17]([OH:19])=O)=[N:12][S:13](=[O:15])(=[O:14])[C:8]=2[CH:7]=1)(=[O:4])=[O:3].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:37]([O:39][C:40]([CH:42]1[CH2:46][CH2:45][CH2:44][CH:43]1[NH:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=1)=[O:41])[CH3:38]>CN(C)C=O>[CH2:37]([O:39][C:40]([CH:42]1[CH2:46][CH2:45][CH2:44][CH:43]1[N:47]([C:17](=[O:19])[CH2:16][C:11]1[NH:10][C:9]2[CH:20]=[CH:21][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][C:8]=2[S:13](=[O:14])(=[O:15])[N:12]=1)[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=1)=[O:41])[CH3:38]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 248585392H-1,2,4-Benzothiadiazine-3-acetic acid, 7-[(methylsulfonyl)amino]-, 1,1-dioxideHCID 57671221HCID 57671221, compound

Product 1

HCID 57671245HCID 57671245, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 1j, 0.10 g, 0.30 mmol) and N,N′-dicyclohexylcarbodiimide (0.068 g, 0.33 mmol) in N,N-dimethylformamide (10 mL) was treated with 2-[(pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester and stirred for 16 h. The mixture was filtered, the filtrate was concentrated in vacuo, and purified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-10% methanol in dichloromethane) to afford the desired product, 2-{[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-pyridin-2-ylmethyl-amino}-cyclopentanecarboxylic acid ethyl ester (0.043 g, 0.076 mmol, 25.3%), as a pale white solid. LC-MS (ESI) calcd for C24H29N5O7S2 563.15, found 564.6 [M+H+].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-56f13e778de64d89bd078c0a6a4ad813
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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