Benzenesulfonamide → HCID 9939093, compound

HRID 1814427Notes

Reaction equation

HRID 1814427 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]2)[CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[CH:4][CH:3]=1.[C:32]1([S:38]([NH2:41])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]2)[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:41][S:38]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:40])=[O:39])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22506170HCID 22506170, compound

Product 1

HCID 9939093HCID 9939093, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[[3-(4-bromophenylureido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (20 mg, 0.041 mmol) and benzenesulfonamide (7.0 mg, 0.045 mmol) in CH2Cl2 (1 ml) were added WSC.HCl (8.6 mg, 0.045 mmol) and DMAP (5.5 mg, 0.045 mmol), and the mixture was stirred at RT for 18 h. The reaction mixture was purified by preparative normal phase HPLC using linear gradients of (A) chloroform and (B) methanol (2-4% B, in 0-2 min; 4-5% B, in 2-6 min; 5% B, in 6-12 min) at a flow rate of 12 ml/min. Fractions containing the major peak were pooled and concentrated to afford 3-[[3-(4-bromophenylureido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]-1-[(phenylsulfonyl)carbamoyl]propane (5.4 mg, 21%): MS(ES+) m/e 627 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 8.05 (m, 2H), 7.50 (m, 3H), 7.44 (d, J=8.8 Hz, 2H), 7.31 (d, J=9.0 Hz, 2H), 7.23 (m, 3H), 7.15 (d, J=7.0 Hz, 1H), 7.02 (m, 1H), 6.92 (m, 1H), 4.72 (m, 1H), 3.73 (m, 1H), 3.58 (m, 1H), 3.21 (m, 1H), 2.96 (m, 1H), 2.79-2.65 (m, 5H), 2.57 (m, 1H), 2.17 (m, 1H), 2.03 (m, 1H), 1.94-1.66 (m, 4H).

Workup

  1. customThe reaction mixture was purified by preparative normal phase
  2. customgradients of (A) chloroform and (B) methanol (2-4% B, in 0-2 min; 4-5% B, in 2-6 min; 5% B, in 6-12 min)
  3. additionFractions containing the major peak
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20600f7bd6a94e71adb3e23d926224ba
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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