1-Pyrrolidineethanamine → HCID 68949185, compound

HRID 2384889Notes

Reaction equation

HRID 2384889 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[S:20][C:14]=3[C:13]2=[O:29])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].[N:30]1([CH2:35][CH2:36][NH2:37])[CH2:34][CH2:33][CH2:32][CH2:31]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[S:20][C:14]=3[C:13]2=[O:29])[CH:9]=[CH:8][C:4]=1[C:5]([NH:37][CH2:36][CH2:35][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:6]

Participants

8

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 689501452-Methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid

Product 1

HCID 68949185HCID 68949185, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Suspend 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-benzoic acid (0.1451 g, 0.35 mmol) in DMF (5 mL) and add 2-pyrrolidin-1-yl-ethylamine (45 mg, 0.39 mmol), EDCI (81 mg, 0.42 mmol), HOBt (57 mg, 0.42 mmol) and Et3N (0.15 mL, 1.06 mmol). Stir the reaction at RT overnight. Dilute with EtOAc (100 mL), wash with water (2×30 mL), and dry over Na2SO4. Purify the crude material by silica gel chromatography, eluting with 2% NH3—H2O, 50% CH3OH/EtOAc to give 9 mg (5%) of the title compound. LC-MS/ES m/z 506.2 [M+H]+.

Workup

  1. customthe reaction at RT overnight
  2. washwash with water (2×30 mL)
  3. dry with materialdry over Na2SO4
  4. customPurify the crude material by silica gel chromatography
  5. washeluting with 2% NH3—H2O, 50% CH3OH/EtOAc

Sources & evidence

ORD record
ord-7af73d3331b341b2854f13ffdfe78e45
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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