Ethylamine → HCID 25000165, compound

HRID 249821Notes

Reaction equation

HRID 249821 reaction equation
[F:1][C:2]1[C:23]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[CH:22][CH:21]=[C:20]([F:38])[C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH:13]=2)[NH:8][CH:7]=1)=[O:5].[CH2:39]([NH2:41])[CH3:40].Cl.CN(C)CCCN=C=NCC>O1CCCC1>[F:1][C:2]1[C:23]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][CH:29]=2)(=[O:26])=[O:27])=[CH:22][CH:21]=[C:20]([F:38])[C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][CH2:16][C:17]([NH:41][CH2:39][CH3:40])=[O:19])[CH:13]=2)[NH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25000164HCID 25000164, compound

Product 1

HCID 25000165HCID 25000165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-{3-[2,6-difluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionic acid (P-0034, 42 mg, 0.076 mmol) dissolved in tetrahydrofuran (3 mL) was added a 2.0 M solution of ethylamine in tetrahydrofuran (110 μL, 0.23 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (29 mg, 0.15 mmol). The reaction mixture was stirred at room temperature for 16 hrs, then extracted with ethyl acetate and water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The desired compound was isolated by silica gel column chromatography (methanol/dichloromethane), with the eluting solvents removed via lyophilizing to provide a white fluffy solid (P-0035, 13 mg, 30%). MS(ESI) [M+H+]+=581.0.

Workup

  1. extractionextracted with ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75698c9fc5bf494381ee9e199a1cb0fe
Source dataset
uspto-grants-2011_01
Patent number
US07863289B2

Reaction notes

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