1,2-Dichloroethane → HCID 66604054, compound

HRID 2410715Notes

Reaction equation

HRID 2410715 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17](O)=[O:18])=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C(Cl)CCl.[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35]>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:28][C:22]1[CH:21]=[C:20]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]3[NH:15][C:14]4[C:9]([C:8]=3[CH:7]=2)=[CH:10][C:11]([C:17]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:18])=[CH:12][CH:13]=4)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 72879MethanesulfonamideHCID 66605267HCID 66605267, compound

Product 1

HCID 66604054HCID 66604054, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-carbamoyl-6-(3-fluoro-4-methoxyphenyl)-9H-carbazole-3-carboxylic acid (53 mg, 0.070 mmol, Example 187) in DMF (1 ml) was added DMAP (63 mg, 0.516 mmol), then EDC (128 mg, 0.668 mmol) and methanesulfonamide (92 mg, 0.967 mmol) and the mixture stirred at room temperature for 18 hours. The reaction mixture was filtered through a 0.45 um Nylon filter and purified by prep HPLC (water/CH3CN/NH4OAc eluent system). Product containing fractions were evaporated to give 17.5 mg 3-(3-fluoro-4-methoxyphenyl)-N6-(methylsulfonyl)-9H-carbazole-1,6-dicarboxamide as an off-white solid. HPLC retention time 11.10 min (HPLC conditions as in Table 9 and Table 10). MS (ESI) m/z [M−H]− 454; [M+H]+ 456. 1H NMR (CD3OD) δ ppm 8.88 (s, 1H), 8.53 (d, 1H, J=1.3), 8.16 (m, 2H), 7.63-7.55 (m, 3H), 7.22 (t, 1H, 8.5), 3.96 (s, 3H), 3.25 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 um Nylon
  2. filtrationfilter
  3. custompurified by prep HPLC (water/CH3CN/NH4OAc eluent system)
  4. additionProduct containing fractions
  5. customwere evaporated

Sources & evidence

ORD record
ord-e15740dbee8d45cb87e33d4cce413adf
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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