Triethylamine → HCID 118159793, compound

HRID 628277Notes

Reaction equation

HRID 628277 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=4)[NH2:19])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C([N:25]([CH2:28]C)CC)C.ClC(Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl.[NH4+].[OH-]>C1COCC1.C(Cl)Cl>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([NH:19][C:28]([NH2:25])=[O:33])[CH:20]=[CH:21][CH:22]=4)[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 94429TriphosgeneHCID 118159464HCID 118159464, compound

Product 1

HCID 118159793HCID 118159793, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)methyl]aniline (16 mg, 0.055 mmol, from Example 43, Step 1) in THF (1.6 mL) and DCM (0.64 mL) were added triethylamine (23 μL, 0.16 mmol) and triphosgene (16 mg, 0.055 mmol, Aldrich). The mixture was stirred for 15 minutes, then NH4OH solution (43 μL, 14.8 N) was added. After stirring for 30 minutes, the product was precipitated as a yellow solid, re-dissolved in MeOH and filtered, then purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (5.5 mg, 30%).

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe product was precipitated as a yellow solid
  3. dissolutionre-dissolved in MeOH
  4. filtrationfiltered
  5. custompurified via preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (5.5 mg, 30%)

Sources & evidence

ORD record
ord-89392f3e81184a04804115854c84ad4d
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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