Triethylamine → HCID 69411964, compound

HRID 1294083Notes

Reaction equation

HRID 1294083 reaction equation
[NH2:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]4[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=4[F:32])=[O:20])=[CH:14][CH:13]=3)=[CH:10][C:4]=2[N:3]=1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>CN(C=O)C.C(Cl)(Cl)Cl>[F:32][C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:29])[F:30])=[CH:27][C:22]=1[NH:21][C:19]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]([S:41]([CH3:40])(=[O:43])=[O:42])[CH:2]([NH2:1])[NH:3][C:4]=3[CH:10]=2)=[CH:17][CH:16]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178508201HCID 178508201, compound2×

Product 1

HCID 69411964HCID 69411964, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 21754633chloroform N,N-dimethylformamideSolvent

Procedure

To a mixture of 2-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenoxy)-1H-benzimidazole (90 mg, 0.20 mmol) (prepared according to similar procedures as described for Intermediates 4, 5, and 6 and Example 22) and triethylamine (30 mg, 0.30 mmol) in DMF/CHCl3 (3 ml/1 ml) was added methanesulfonyl chloride (30 mg, 0.26 mmol). After stirring for 3 h at rt, the reaction mixture was washed with water and extracted with CHCl3. The organic layer was dried over MgSO4 and evaporated. The crude material was purified with silica gel column chromatography (AcOEt) to give the product of Example 23 (11.0 mg, 11%) and the title compound (34 mg, 25%): 1H NMR (DMSO-d6) δ 9.14 (s, 1H), 8.85 (s, 1H), 8.62 (d, 1H), 7.51 (d, 1H), 7.47 (d, 1H), 7.46 (d, 2H), 7.38 (m, 1H), 7.02 (brs, 2H), 6.97 (d, 2H), 6.82 (d, 1H), 6.70 (dd, 1H), 3.49 (s, 3H); MS m/e 524 (M+1).

Workup

  1. washthe reaction mixture was washed with water
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe crude material was purified with silica gel column chromatography (AcOEt)

Sources & evidence

ORD record
ord-ffbb129e0df64668b67bd5eb06dde1c3
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

Loading…