Acetic Acid → HCID 137194574, compound

HRID 731252Notes

Reaction equation

HRID 731252 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[N:11]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[C:12](=[O:31])[CH2:13][C:14]1[NH:19][C:18]2[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:17]=2[S:16](=[O:30])(=[O:29])[N:15]=1)=O)C.[O-]CC.[Na+].C(O)(=O)C>C(O)C>[CH3:35][N:34]([CH3:36])[CH2:33][CH2:32][N:11]1[C@@H:7]2[C@@H:6]([CH2:10][CH2:9][CH2:8]2)[C:4]([OH:3])=[C:13]([C:14]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][C:17]=3[S:16](=[O:29])(=[O:30])[N:15]=2)[C:12]1=[O:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 576712222-{(2-Dimethylamino-ethyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 137194574HCID 137194574, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-{(2-dimethylamino-ethyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclopentanecarboxylic acid ethyl ester (25.4 mg, 0.047 mmol) in ethanol (2 mL) was treated with a 21% w/w solution of sodium ethoxide in ethanol (0.070 mL) and stirred for 2 h at 60° C. Glacial acetic acid (0.100 mL) was added, the solvents were removed in vacuo, and the crude material was purified by prep-HPLC [Column Luna 5μ C18 (2) 100 Å AXIA 50×21.2 mm, 5 micron, 30%-90% in 7 min @ 30 mL/min flow rate, 0.05% trifluoroacetic acid in acetonitrile/0.05% trifluoroacetic acid in water] to afford the desired product, cis-N-{3-[1-(2-dimethylamino-ethyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (5.7 mg, 0.011 mmol, 23.4%), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.53-1.67 (3H, m), 2.02-2.19 (3H, m), 2.88 (6H, s), 3.07 (3H, s), 3.24-3.33 (2H, m), 3.38-3.45 (2H, m), 3.92-3.98 (1H, m), 4.08-4.15 (1H, m), 7.52-7.58 (3H, m), 9.27 (1H, s), 10.20 (1H, s). LC-MS (ESI) calcd for C20H27N5O6S2 497.14, found 498.3 [M+H+].

Workup

  1. customthe solvents were removed in vacuo
  2. customthe crude material was purified by prep-HPLC [Column Luna 5μ C18 (2) 100 Å AXIA 50×21.2 mm, 5 micron, 30%-90% in 7 min

Sources & evidence

ORD record
ord-280d0b1e984f4373bd0a786d013a5cc0
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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