4-Methylmorpholine → HCID 21893751, compound

HRID 1244170Notes

Reaction equation

HRID 1244170 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][N:18]([S:21]([C:24]4([C:30]([O:32]C(C)(C)C)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)(=[O:23])=[O:22])[CH2:17][CH2:16]3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[OH:37][N:38]1C2C=CC=CC=2N=N1.CN1CCOCC1.O1CCCCC1ON.[ClH:62].CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:1][OH:2].[C:30]([O-:32])(=[O:31])[CH3:24].[ClH:62].[OH:37][NH:38][C:30]([C:24]1([S:21]([N:18]2[CH2:17][CH2:16][N:15]([C:12]3[N:13]=[CH:14][C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:10][N:11]=3)[CH2:20][CH2:19]2)(=[O:23])=[O:22])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[O:31]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 21069274HCID 21069274, compound

Product 2

HCID 21893751HCID 21893751, compoundYield 5%HCID 21931235HCID 21931235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the tert-butyl 4-({4-[5-(4-methoxyphenyl)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)tetrahydro-2H-pyran-4-carboxyate acid trifluoroacetate product from Part C (266 mg, 0.57 mmol), N-hydroxybenzotriazole (97.2 mg, 0.72 mmol), 4-methylmorpholine (0.20 mL, 1.8 mmol), O-tetrahydro-2H-pyran-2-yl-hydroxyamine (105 mg, 0.9 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (161 mg, 0.84 mmol) in DMF (11 mL) was stirred at ambient temperature under an argon atmosphere for 18 hr. Afterward, the solution was concentrated in vacuo, diluted with water (20 mL), and extracted with ethyl acetate. The organic layer was washed with water, washed with saturated NaCl, dried over MgSO4, and concentrated in vacuo to produce a solid. Chromatography (on silica, 5% methanol/acetate) produced the desired compound in the form of a solid (128 mg, 39%). MS H+ calculated for C26H35N5SO7: 562; found: 562.20

Workup

  1. concentrationAfterward, the solution was concentrated in vacuo
  2. additiondiluted with water (20 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. washwashed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto produce a solid

Sources & evidence

ORD record
ord-a442369171814610a7abf06c16df464e
Source dataset
uspto-grants-2006_10
Patent number
US07119203B2

Reaction notes

Loading…