Triethylamine → 4-((2Rs)-bicyclo(2.2.1)hept-2-ylamino)-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

HRID 2085670Notes

Reaction equation

HRID 2085670 reaction equation
Cl[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].Cl.[NH2:31][CH:32]1[CH2:37][CH:36]2[CH2:38][CH:33]1[CH2:34][CH2:35]2.C(N(CC)CC)C>CN(C=O)C>[CH:33]12[CH2:38][CH:36]([CH2:35][CH2:34]1)[CH2:37][CH:32]2[NH:31][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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 518934Endo-bicyclo[2.2.1]heptan-2-amine hydrochlorideHCID 102249074-Chloro-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

Product 1

HCID 102791324-((2Rs)-bicyclo(2.2.1)hept-2-ylamino)-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1D (50 mg, 0.12 mmol), 2-aminonorbornane hydrochloride (106 mg, 0.58 mmol), and triethylamine (0.08 ml, 0.58 mmol) in DMF (2 mL) were heated to 120° C. in a sealed vial with shaking for 16 hours, then concentrated. The concentrate was dissolved in 1:1/DMSO:methanol (1.0 ml) and purified by reverse phase preparative HPLC with 0.1% TFA in H2O/CH3CN to provide the desired product. MS (APCI(+)) m/e 510 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ12.45 (br s, 1H), 8.67 (d, 1H), 8.48 (d, 1H), 7.99 (dd, 1H), 7.95 (d, 2H), 7.78 (2d, 4H), 7.32 (t, 2H), 7.24 (d, 1H), 4.04 (m, 1H), 2.58 (m, 1H), 2.27 (m, 1H), 2.24-2.21 (m, 1H), 1.59-1.29 (m, 6H), 0.97 (dt, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in 1:1/DMSO
  3. custommethanol (1.0 ml) and purified by reverse phase preparative HPLC with 0.1% TFA in H2O/CH3CN

Sources & evidence

ORD record
ord-df00db6e36f64d75a8e7cdfee2ae3492
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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