1-Hydroxybenzotriazole → HCID 46897098, compound

HRID 1808375Notes

Reaction equation

HRID 1808375 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([OH:25])=O)[CH:20]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[CH:27]([N:30]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH3:32])([CH3:29])C.[CH:36]1[CH:37]=[CH:38][C:39]2[N:44](O)N=NC=2[CH:41]=1.C[CH2:47][N:48]=[C:49]=NCCCN(C)C.Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:26])[C:6]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH2:22][C:23]([N:44]4[CH2:41][CH2:36][C:37]5([CH2:29][CH2:27][N:30]([C:33]6[CH:34]=[CH:49][N:48]=[CH:47][CH:35]=6)[CH2:31][CH2:32]5)[CH2:38][CH2:39]4)=[O:25])[CH:20]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59483826HCID 59483826, compound

Product 1

HCID 46897098HCID 46897098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-6-yl)acetic acid (E-19) (150 mg, 0.4 mmol) in dichloromethane (10 ml/mmol) there was added at 0° C. diisopropylethylamine (0.3 ml, 1.6 mmol) followed by HOBT (54 mg, 0.48 mmol) and EDCl (115 mg, 0.6 mmol). The resulting reaction mixture was stirred for 16 h at 25° C. and then diluted with dichloromethane (30 ml) and washed with saturated ammonium chloride solution, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution. Drying (Na2SO4) and concentration in vacuo were then carried out. The resulting crude product was purified by column chromatography (Alox-neutral, 0.5% methanol in dichloromethane). Yield: 150 mg (64%). MS, Rt=3.4 min; m/z=589.4 [MH]+

Workup

  1. customThe resulting reaction mixture
  2. washwashed with saturated ammonium chloride solution, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution
  3. customDrying
  4. concentration(Na2SO4) and concentration in vacuo
  5. customThe resulting crude product was purified by column chromatography (Alox-neutral, 0.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b48a80a02fe44ed686aa9536725b3c4f
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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