Triethylamine → HCID 178426935, compound

HRID 2352932Notes

Reaction equation

HRID 2352932 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:39]=[CH:40][CH:41]=2)[C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19](=[CH:25][NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:29][CH:28]=4)[C:20](=[O:24])[NH:21]3)=[CH:17][CH:16]=2)=[O:14])=[O:8])=[CH:5][C:4]([CH3:42])=[N:3]1.[CH2:43]1[CH2:47]N([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:44]1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CON>CN(C=O)C>[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:39]=[CH:40][CH:41]=2)[C:13]([C:15]2[CH:23]=[C:22]3[C:18](/[C:19](=[CH:25]/[NH:26][C:27]4[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH:43]([CH3:47])[CH3:44])=[O:37])=[CH:29][CH:28]=4)/[C:20](=[O:24])[NH:21]3)=[CH:17][CH:16]=2)=[O:14])=[O:8])=[CH:5][C:4]([CH3:42])=[N:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2724699PyBOPHCID 178426934HCID 178426934, compound

Product 1

HCID 178426935HCID 178426935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a dry 50 mL round bottomed flask, 4-{4-[(6-{3-[(2,5-Dimethyl-2H-pyrazole-3-carbonyl)-amino]-benzoyl}-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-amino]-phenyl}-butyric acid (as prepared in Example 324, 50 mg, 0.088 mmol) was dissolved into DMF (1 mL), under Ar(g). PyBOP (60 mg, 0.115 mmol) was then added followed by triethyl amine (0.04 mL, 0.266 mmol) and O-methylhydroxylamine hydrochloride (22 mg, 0.264 mmol). The mixture was stirred at room temperature for 2 h after which the reaction mixture was partitioned between EtOAc (˜10 mL) and brine (˜10 mL). The organic layer was extracted with brine (3ט10 mL). The organic layers were combined and then concentrated in vacuo. The crude mixture was then chromatographed over silica (EtOAc/MeOH gradiant was used starting from 1% MeOH up to 5% MeOH). The title compound was isolated in pure form as a yellow solid (27.8 mg, 0.046 mmol, 53%).

Workup

  1. customwas partitioned between EtOAc (˜10 mL) and brine (˜10 mL)
  2. extractionThe organic layer was extracted with brine (3ט10 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture was then chromatographed over silica (EtOAc/MeOH gradiant

Sources & evidence

ORD record
ord-ee7bb167c1ab4ce3abc7964832b3d3f6
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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