1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131736432, compound

HRID 1056561Notes

Reaction equation

HRID 1056561 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:34]([NH:41][C@@H:42]([CH:46]([CH3:48])[CH3:47])[C:43](O)=[O:44])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([N:26]([C:43](=[O:44])[C@@H:42]([NH:41][C:34](=[O:35])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:46]([CH3:48])[CH3:47])[S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 83693Boc-L-ValineHCID 42611257Vemurafenib

Product 1

HCID 131736432HCID 131736432, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.3 g, 0.61 mmol), (S)-2-(Boc-amino)-3-methylbutyric acid (0.28 g, 1.29 mmol) and 4-ppy (9 mg, 0.06 mmol) in DMF (2 mL) was added EDCI (234 mg, 1.23 mmol). The reaction was stirred at rt for 16 h, then diluted with EtOAc (30 mL) and washed with water (30 mL×3). The mixture was dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=3/1 to 2/1) to afford the title compound as a white solid (41 mg, 29.1%). The title compound was characterized by LC-MS as shown below:

Workup

  1. washwashed with water (30 mL×3)
  2. dry with materialThe mixture was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=3/1 to 2/1)

Sources & evidence

ORD record
ord-eb10559cc66640beb67e0c6ba03b19d1
Source dataset
uspto-grants-2016_07
Patent number
US09399639B2

Reaction notes

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