Triethylamine → HCID 136358520, compound

HRID 601425Notes

Reaction equation

HRID 601425 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:28])[N:14]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:15]4[C:20]([C:21]=3[OH:22])=[CH:19][CH:18]=[CH:17][N:16]=4)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.Cl[S:32]([N:35]1[CH2:39][CH2:38][CH2:37][C@H:36]1[C:40]([O:42][CH3:43])=[O:41])(=[O:34])=[O:33].C(N(CC)CC)C>C(#N)C>[OH:22][C:21]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:13](=[O:28])[C:12]=1[C:7]1[NH:6][C:5]2[CH:29]=[CH:30][C:2]([NH:1][S:32]([N:35]3[CH2:39][CH2:38][CH2:37][C@H:36]3[C:40]([O:42][CH3:43])=[O:41])(=[O:33])=[O:34])=[CH:3][C:4]=2[S:9](=[O:11])(=[O:10])[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10036702159525-92-5HCID 1354307103-(7-Amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 136358520HCID 136358520, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

The product of Example 205 (0.030 g, 0.0703 mmol) in acetonitrile (2 ml) was treated with the product of Example 461A (0.018 g, 0.077 mmol) and triethylamine (0.011 ml, 0.077 mmol), stirred at 60° C. for 20 hours and cooled to about 25° C. The solvent was evaporated under reduced pressure, and the residue was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/10 mM ammonium acetate in water over 8 minutes (10 minutes run time) at a flow rate of 40 mL/min give the title compound (7 mg, 16%). 1H NMR (300 MHz, DMSO-d6) δ 0.99 (d, J=6.25 Hz, 6 H) 1.59 (m, 2 H) 1.67 (m, 2 H) 1.87 (m, 4 H) 2.09 (d, J=8.46 Hz, 1 H) 3.60 (s, 3 H) 4.26 (dd, J=8.64, 3.86 Hz, 1 H) 4.50 (m, 2 H) 7.55 (m, 4 H) 7.73 (d, J=8.82 Hz, 1 H) 8.57 (dd, J=8.09, 1.84 Hz, 1 H) 8.90 (dd, J=4.78, 1.84 Hz, 1 H) 10.53 (s, 1 H) 14.07 (s, 1 H). MS (ESI−) m/z 617 (M−H)−.

Workup

  1. temperaturecooled to about 25° C
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  4. customover 8 minutes
  5. custom(10 minutes run time)

Sources & evidence

ORD record
ord-d2d3031e8c62413daf46693fef56d033
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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