Triethylamine → HCID 56925644, compound

HRID 2175455Notes

Reaction equation

HRID 2175455 reaction equation
[CH2:1]([C:3]1([CH3:21])[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[O:4]1)[CH3:2].CCN(CC)CC.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([S:39](Cl)(=[O:41])=[O:40])[CH:34]=[CH:35][C:36]=1[O:37][CH3:38].[NH4+].[Cl-]>C(Cl)Cl>[CH2:1]([C:3]1([CH3:21])[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:39]([C:33]3[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([O:30][CH3:29])[CH:32]=3)(=[O:41])=[O:40])[CH:9]=2)[O:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 56925643HCID 56925643, compound

Product 1

HCID 56925644HCID 56925644, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9 (80 mg, 0.29 mmol) in DCM (3 mL) was added Et3N (0.12 mL, 0.85 mmol) and 3,4-dimethoxybenzenesulfonyl chloride (135 mg, 0.573 mmol). After 24 h, sat. NH4Cl was added to the reaction mixture and the aqueous layer was extracted with DCM (5×2 mL). The organic layers was combined, dried over MgSO4 and concentrated under vacuum. The crude product was purified by column (silica gel, 5:1 Hx/EtOAc) to give a white solid (42.6 mg). Yield: 32%. 1H NMR (CDCl3): δ 7.35 (dd, J=6.4 Hz, 2.0 Hz, 1H), 7.25-7.23 (m, 3H), 7.02-6.98 (m, 3H), 6.94 (d, J=8.4 Hz, 1H), 6.91-6.88 (m, 2H), 4.62 (s, 2H), 3.98 (s, 3H), 3.77 (s, 3H), 1.71-1.65 (m, 2H), 1.43 (s, 3H), 0.94 ppm (t, J=7.6 Hz, 3H). 13C NMR (CDCl3): δ 152.8, 152.5, 148.7, 139.2, 130.5, 129.8, 129.3, 129.2, 128.8, 127.9, 127.8, 126.6, 122.8, 121.4, 121.1, 115.8, 110.4, 79.0, 56.2, 56.1, 54.3, 34.0, 26.0 ppm. MS (ESI) m/z 502 [(M+Na)+]. HPLC: ret. time=5.9 min, 98.9%.

Workup

  1. extractionthe aqueous layer was extracted with DCM (5×2 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by column (silica gel, 5:1 Hx/EtOAc)

Sources & evidence

ORD record
ord-125985795e284ef5aae6dc48bd4e2f33
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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