Pyridine → (3-{[Methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-carbamic acid phenyl ester

HRID 1685048Notes

Reaction equation

HRID 1685048 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH2:7][N:8]([CH3:16])[C:9]([C@H:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[O:10])[N:3]=1.N1C=CC=CC=1.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C(Cl)Cl>[C:27]1([O:26][C:24](=[O:25])[NH:1][C:2]2[S:6][N:5]=[C:4]([CH2:7][N:8]([CH3:16])[C:9]([C@H:11]3[CH2:15][CH2:14][CH2:13][O:12]3)=[O:10])[N:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 66662881(R)-tetrahydro-furan-2-carboxylic acid (5-amino-[1,2,4]thiadiazol-3-ylmethyl)-methyl-amide2×

Product 1

HCID 58055093(3-{[Methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step 2, (R)-tetrahydro-furan-2-carboxylic acid (5-amino-[1,2,4]thiadiazol-3-ylmethyl)-methyl-amide (3.0 g, 12.4 mmol), and pyridine (1.08 g, 13.6 mmol) in DCM (120 mL) was added phenyl chloroformate (1.95 g, 12.4 mmol) by syringe at 0 C under N2. The reaction mixture was stirred at room temperature overnight, concentrated and purified by silica gel column chromatography (PE:EA=1:1) to afford Intermediate 39: (3-{[methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-carbamic acid phenyl ester (3.0 g, yield: 67%) as a pale solid. LC-MS (m/z): 363.1 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-55a89727a6fe4445ad740351d643a877
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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