Hydrochloric Acid → cis-2-{(2-Cyclopropylethyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclopentanecarboxylic acid ethyl ester

HRID 731290Notes

Reaction equation

HRID 731290 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[NH:11][CH2:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)=[O:5])[CH3:2].[CH3:17][S:18]([NH:21][C:22]1[CH:37]=[CH:36][C:25]2[NH:26][C:27]([CH2:32][C:33](O)=[O:34])=[N:28][S:29](=[O:31])(=[O:30])[C:24]=2[CH:23]=1)(=[O:20])=[O:19].Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[N:11]([CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16]1)[C:33](=[O:34])[CH2:32][C:27]1[NH:26][C:25]2[CH:36]=[CH:37][C:22]([NH:21][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:23][C:24]=2[S:29](=[O:30])(=[O:31])[N:28]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 248585392H-1,2,4-Benzothiadiazine-3-acetic acid, 7-[(methylsulfonyl)amino]-, 1,1-dioxideHCID 69063495cis-2-(2-Cyclopropylethylamino)-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 69063423cis-2-{(2-Cyclopropylethyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclopentanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of cis-2-(2-cyclopropylethylamino)-cyclopentanecarboxylic acid ethyl ester (42.7 mg, 0.189 mmol) in N,N-dimethylformamide (3.0 mL) was added (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 1j, 94.8 mg, 0.284 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (73.9 mg, 0.378 mmol), and 4-dimethylaminopyridine (5.8 mg, 0.047 mmol). After stirring at 25° C. for 14 h, the mixture was diluted with ethyl acetate and acidified with 1.0 M aqueous hydrochloric acid solution. The layers were separated and the organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, cis-2-{(2-cyclopropylethyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclopentanecarboxylic acid ethyl ester, as a yellowish oil. The crude product was used in the next step without further purification. LC-MS (ESI) calcd for C23H32N4O7S2 540.17, found 541.4 [M+H+].

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fd4390e44b143e09488d3493d51dc50
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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