4-Methylmorpholine → HCID 135955951, compound

HRID 731301Notes

Reaction equation

HRID 731301 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][NH:6][C@H:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12]([O:14]C)=O.[CH3:19][S:20]([NH:23][C:24]1[CH:39]=[CH:38][C:27]2[NH:28][C:29]([CH2:34][C:35](O)=[O:36])=[N:30][S:31](=[O:33])(=[O:32])[C:26]=2[CH:25]=1)(=[O:22])=[O:21].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[OH:14][C:12]1[C@H:8]2[C@H:7]([CH2:11][CH2:10][CH2:9]2)[N:6]([CH2:5][C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([CH3:1])[CH:3]=2)[C:35](=[O:36])[C:34]=1[C:29]1[NH:28][C:27]2[CH:38]=[CH:39][C:24]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:25][C:26]=2[S:31](=[O:33])(=[O:32])[N:30]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 248585392H-1,2,4-Benzothiadiazine-3-acetic acid, 7-[(methylsulfonyl)amino]-, 1,1-dioxideHCID 57671188HCID 57671188, compound

Product 1

HCID 135955951HCID 135955951, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of methyl (1R,2S)-2-[(3-methylbenzyl)amino]cyclopentane-carboxylate (74 mg, 0.30 mmol) and (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 1j, 100 mg, 0.30 mmol) in anhydrous N,N-dimethylformamide (3 mL) under a nitrogen atmosphere, N-methylmorpholine (0.10 mL, 0.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (63 mg, 0.33 mmol) were added sequentially. The mixture was stirred at 25° C. for 16 h, diluted with ethyl acetate, washed with 1.0 M aqueous hydrochloric acid 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 1.0 M aqueous hydrochloric acid 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-167ca2a967db4fda9a68c9e71f2ce23f
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

Loading…