2,3-Dimethylbenzoic acid → HCID 22884150, compound

HRID 1598452Notes

Reaction equation

HRID 1598452 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:14][CH2:15][S:16][CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:19]=2[CH3:18])[CH2:10][C@@H:9]1[CH2:14][CH2:15][S:16][CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22884133HCID 22884133, compound

Product 1

HCID 22884150HCID 22884150, compoundYield 88.9%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the procedure described for Example 1, Step A except using 1-tert-butoxycarbonyl-2(S)-(2-methylthioethyl)piperazine (1.87 g, 7.19 mmol), 2,3-dimethylbenzoic acid (1.08 g, 7.19 mmol), HOBT (0.970 g, 7.19 mmol), EDC.HCl (1.64 g, 8.62 mmol) in methylene chloride (50 mL). Triethylamine was added to adjust the pH to 7. Chromatography on silica gel with 30% ethyl acetate in hexane afforded the title compound as a clear oil (2.51 g). NMR (DMSO-d6, 300 MHz) δ 6.9-7.3 (3H, m), 4.22-4.50 (2H, mm), 3.62-4.06 (2H, mm), 2.66-3.24 (4H, mm), 2.4 (1H, m), 2.24 (3H, s), 1.92-2.18 (6H, ms),1.4-1.8 (2H, m), 1.39 (9H, s).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a4c02a59e6954144ae9ba3ba083d8753
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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