Hydrochloric Acid → n-(4-((((4'-Fluoro-1,1'-biphenyl-4-yl)carbonyl)amino)sulfonyl)-2-nitrophenyl)adamantane-1-carboxamide

HRID 2356114Notes

Reaction equation

HRID 2356114 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[H-].[Na+].[C:32]12([C:42](Cl)=[O:43])[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[CH2:33]1)[CH2:39]2.Cl>C1COCC1.O1CCOCC1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:42]([C:32]45[CH2:41][CH:36]6[CH2:35][CH:34]([CH2:40][CH:38]([CH2:37]6)[CH2:39]4)[CH2:33]5)=[O:43])=[C:3]([N+:27]([O-:29])=[O:28])[CH:4]=3)(=[O:10])=[O:9])=[O:13])=[CH:19][CH:18]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 989151-Adamantanecarbonyl chlorideHCID 227303564-Amino-n-((4'-fluoro-1,1'-biphenyl-4-yl)carbonyl)-3-nitrobenzenesulfonamide

Product 1

HCID 22730319n-(4-((((4'-Fluoro-1,1'-biphenyl-4-yl)carbonyl)amino)sulfonyl)-2-nitrophenyl)adamantane-1-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 380A (101 mg, 0.25 mmol) in THF (3 mL) was treated with 60% sodium hydride in oil (40 mg, 1.0 mmol), stirred for 30 minutes, treated with 1-adamantanecarbonyl chloride (60 mg, 0.30 mmol), stirred for 30 minutes, adjusted to pH<7 with 4M HCl in dioxane (0.5 mL), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 576 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.23 (s, 1H), 8.52 (d, 1H), 8.23 (dd, 1H), 8.19 (d, 1H), 7.95 (d, 2H, 7.75 (r, 4H), 7.31 (tt, 2H), 2.05 (3s, 3H), 1.90 (m, 6H), 1.70 (m, 6H).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0c1c9b03c70a4803866749cb91523767
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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