Triethylamine → HCID 67951138, compound

HRID 923642Notes

Reaction equation

HRID 923642 reaction equation
I[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[S:16]1(=O)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2N=C1.CC[N:28]([CH2:31]C)CC.C([O-])([O-])=[O:34].[Cs+].[Cs+]>C(Cl)Cl>[O:34]=[C:31]1[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:16][N:28]1[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 53400715BenzothiazolinoneHCID 67811489HCID 67811489, compound

Product 1

HCID 67951138HCID 67951138, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-(2-iodoacetyl)piperazine-1-carboxylate (200 mg, 0.61 mmol) was added to a suspension of benzothiazolone 1 (102 mg, 0.67 mmol), Et3N (233 mg, 1.83 mmol) and Cs2CO3 (198 mg, 0.61 mmol) in anhydrous CH2Cl2 (8 mL) at room temperature. The mixture was stirred for 26 h, and washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:2) to give the title compound (134 mg, 63% yield). The purity of product was 99.3% as shown by HPLC on an HC-C18 column (Agilent, 4.6×250 mm, 5 μM), tR=11.87 min (gradients of 20-90% aqueous CH3CN in 20 min). C16H19N3O4S; white solid; mp 158-160° C.; 1H NMR (400 MHz, CDCl3) δ 8.09 (1H, dd, J=7.2 Hz, 0.8 Hz), 7.59 (1H, m), 7.53 (1H, dd, J=7.2, 0.8 Hz), 7.38 (1H, m), 4.69 (2H, s), 4.13 (2H, q, J=7.2 Hz), 3.60 (2H, m), 3.55 (2H, m), 3.48 (4H, m), 1.25 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 164.6, 154.6, 140.8, 131.8, 130.0, 126.4, 125.1, 122.9, 120.0, 61.9, 45.3, 45.0, 43.5 (2×), 42.2, 15.0; ESI-HRMS calcd for C16H19N3O4S: 372.0994. found: m/z 372.0992 [M+H]+.

Workup

  1. washwashed with 1 M HCl(aq)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:2)

Sources & evidence

ORD record
ord-f15982f72d214fa3b23367c98640efb2
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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