Pyrrolidine → HCID 15407417, compound

HRID 1856824Notes

Reaction equation

HRID 1856824 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:15][C:6]2=[C:7]([C:12]([OH:14])=O)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:16])[CH2:3]1.Cl.CN(C)[CH2:21][CH2:22][CH2:23][N:24]=[C:25]=NCC.N1CCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:17][C:2]1([CH3:1])[CH2:15][C:6]2=[C:7]([C:12]([N:24]3[CH2:25][CH2:21][CH2:22][CH2:23]3)=[O:14])[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:16])[CH2:3]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2819767SBB053495

Product 1

HCID 15407417HCID 15407417, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid (1.0 g, 3.7 mmol), 4-dimethylaminopyridine (0.75 g, 6.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g, 6 mmol) in DCM (30 mL) was added pyrrolidine (0.34 mL, 4.1 mmol). The mixture was stirred for 18 h then the solution was evaporated and the residue partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was separated, washed with 1M HCl (2×20 mL) and sat. K2CO3 (20 mL). The organic layer was separated, dried (MgSO4) and evaporated. The residue was triturated with hexane/ether to afford the title amide (905 mg, 76%) as a colourless solid. mp 153-155° C. C16H21NO2S2 requires: C, 59.41; H, 6.54; N, 4.33%. Found: C, 59.70; H, 6.73; N, 4.77%, 1H NMR (360 MHz, CDCl3) δ1.05 (6H, s), 1.94-2.04 (4H, m), 2.40 (2H, s), 2.59 (3H, s), 2.84 (2H, s), 3.59-3.62 (4H, m). MS (ES+) 324 (M+1).

Workup

  1. customthe solution was evaporated
  2. customthe residue partitioned between EtOAc (20 mL) and water (20 mL)
  3. customThe organic layer was separated
  4. washwashed with 1M HCl (2×20 mL) and sat. K2CO3 (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was triturated with hexane/ether

Sources & evidence

ORD record
ord-1b948bddb32d433a8fe154208168b1ff
Source dataset
uspto-grants-2000_11
Patent number
US06143773

Reaction notes

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