Acetic Acid → HCID 137194572, compound

HRID 731245Notes

Reaction equation

HRID 731245 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[N:11]([C:19](=[O:38])[CH2:20][C:21]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][C:24]=2[S:23](=[O:37])(=[O:36])[N:22]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=O)C.[O-]CC.[Na+].C(O)(=O)C>C(O)C>[OH:3][C:4]1[C@H:6]2[C@H:7]([CH2:8][CH2:9][CH2:10]2)[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:19](=[O:38])[C:20]=1[C:21]1[NH:26][C:25]2[CH:27]=[CH:28][C:29]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][C:24]=2[S:23](=[O:37])(=[O:36])[N:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 57671245HCID 57671245, compound

Product 1

HCID 137194572HCID 137194572, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-{[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-pyridin-2-ylmethyl-amino}-cyclopentanecarboxylic acid ethyl ester (0.043 g, 0.076 mmol) in ethanol (5 mL) was treated with a 21% w/w solution of sodium ethoxide in ethanol (0.114 mL) and stirred for 16 h at 60° C. Glacial acetic acid (0.100 mL) was added, the solvents were removed in vacuo, and the residue 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-(4-hydroxy-2-oxo-1-pyridin-2-ylmethyl-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 (8.7 mg, 0.017 mmol, 22.4%), as a pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.47-1.71 (3H, m), 1.99-2.15 (3H, m), 3.06 (3H, s), 3.97-4.03 (1H, m), 4.61-4.65 (1H, m), 4.99 (1H, d, J=15.3 Hz), 7.32-7.35 (1H, m), 7.42 (1H, d, J=7.8 Hz), 7.49-7.52 (1H, m), 7.56-7.58 (2H, m), 7.80-7.84 (1H, m), 8.54 (1H, d, J=4.7 Hz), 10.18 (1H, s). LC-MS (ESI) calcd for C22H23N5O6S2 517.11, found 518.1 [M+H+].

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue 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-687f5958fb7a426387d59cd52600c940
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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