Triethylamine → HCID 68770690, compound

HRID 2265291Notes

Reaction equation

HRID 2265291 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH:4]([NH:15][C:16](=[O:37])[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[NH:24][S:25]([C:28]1[C:33]2=[N:34][S:35][N:36]=[C:32]2[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)O.CCN(CC)CC.CS([Cl:50])(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:38])[C:4]([NH:15][C:16](=[O:37])[C:17]1[CH:22]=[C:21]([Cl:50])[C:20]([Cl:23])=[CH:19][C:18]=1[NH:24][S:25]([C:28]1[C:33]2=[N:34][S:35][N:36]=[C:32]2[CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])=[CH:5][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68768583HCID 68768583, compound

Product 1

HCID 68770690HCID 68770690, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-3-hydroxy-propionic acid methyl ester (42 mg, 0.068 mmol) in DCM (1.5 mL) was added Et3N (38 μL, 0.273 mmol) and the mixture was cooled to 0° C. MsCl (8 μL, 0.102 mmol) was added and the mixture was warmed to rt and stirred for 1.5 h. The mixture was heated to 50° C., treated with catalytic DMAP, and stirred overnight. The mixture was diluted with satd. aq. NaHCO3 and extracted with DCM (3×). The combined organic layers were dried (MgSO4) and concentrated to provide 2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoylamino]-3-(3,4-dichloro-phenyl)-acrylic acid methyl ester. The crude product was hydrolyzed as in EXAMPLE 2, Part E, to provide the title compound (25% for two steps). HPLC: RT=9.97 min. MS (ESI−): mass calcd. for C22H15Cl3N4O5S2, 618.30; m/z found, 581/583 [M−H]−. 1H NMR (400 MHz, acetone-d6): 11.82 (s, 1H), 9.37 (d, J=5.1, 1H), 8.48 (d, J=7.1, 1H), 8.34 (dd, J=8.8, 0.9, 1H), 7.96-7.86 (m, 2H), 7.82-7.75 (m, 2H), 7.64-7.55 (m, 3H), 7.11 (dd, J=8.5, 2.0, 1H).

Workup

  1. temperaturethe mixture was warmed to rt
  2. temperatureThe mixture was heated to 50° C.
  3. stirringstirred overnight
  4. additionThe mixture was diluted with satd
  5. extractionaq. NaHCO3 and extracted with DCM (3×)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e9850032dac44e6b30c26ae159987e8
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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