4-Methylmorpholine → HCID 25221636, compound

HRID 453612Notes

Reaction equation

HRID 453612 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:10]([CH2:19][C:20](O)=[O:21])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:25][N:26]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.ON.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:10]([CH2:19][C:20]([NH:26][OH:25])=[O:21])[CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2829056HCID 2829056, compound

Product 1

HCID 25221636HCID 25221636, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 30 mg (0.08 mmol) of 1, 11 mg (0.08 mmol) of N-hydroxybenzotriazole (HOBt), 21 mg (0.11 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI.HCl), and 28 mL (0.25 mmol) of 4-methylmorpholine in 5 mL dry CH2Cl2 was added 6 mg (0.08 mmol) of HONH2.HCl at room temperature. The resulting mixture was stirred overnight and washed with 5 mL of H2O. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc) to give 6 mg (20%) of 2 as a white viscous residue that solidified slowly at room temperature: 1H NMR (400 MHz, DMSO-d6) δ 10.69 (s, 1H), 8.90 (brs, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.72 (s, 1H), 7.68-7.50 (m, 7H), 3.39 (s, 2H); 13C NMR (100 MHz, DMSO-d6) 185.9, 166.3, 148.8, 139.7, 138.6, 137.4, 136.0, 133.0, 132.3, 130.6, 129.2, 129.2, 129.1, 128.9; IR (KBr) cm−1 3305, 3223, 3060, 2921, 1746, 1631, 1436; LREIMS C19H14ClNO3S requires 371.04. Found: 371 ([M+], 9%), 355 (100%).

Workup

  1. washwashed with 5 mL of H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-59aa59f244c84b2cb9b88008ce740c28
Source dataset
uspto-grants-2013_07
Patent number
US08492428B2

Reaction notes

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