Triethylamine → HCID 118159540, compound

HRID 628417Notes

Reaction equation

HRID 628417 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[NH:15]1[CH2:18][CH:17]([N:19]2[CH:23]=[CH:22][C:21]([C:24]3[N:36]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=4)[C:27]4[CH:28]=[CH:29][C:30]5[N:31]([C:32]([CH3:35])=[N:33][N:34]=5)[C:26]=4[CH:25]=3)=[N:20]2)[CH2:16]1.C(N(CC)CC)C.[CH3:52][N:53]([CH3:58])[S:54](Cl)(=[O:56])=[O:55]>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:44][C:40]1[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=1)[CH2:37][N:36]1[C:27]2[CH:28]=[CH:29][C:30]3[N:31]([C:32]([CH3:35])=[N:33][N:34]=3)[C:26]=2[CH:25]=[C:24]1[C:21]1[CH:22]=[CH:23][N:19]([CH:17]2[CH2:16][N:15]([S:54]([N:53]([CH3:58])[CH3:52])(=[O:56])=[O:55])[CH2:18]2)[N:20]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 118159861HCID 118159861, compound

Product 1

HCID 118159540HCID 118159540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(1-azetidin-3-yl-1H-pyrazol-3-yl)-6-(3-chlorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine bis(trifluoroacetate) salt (10.2 mg, 0.0158 mmol, prepared as in Example 156) in DCM (0.56 mL) was treated with triethylamine (11 μL, 0.079 mmol) and dimethylsulfamoyl chloride (2.5 μL, 0.024 mmol, Aldrich) and stirred for 35 minutes. Additional triethylamine (4.4 μL, 0.032 mmol) and dimethylsulfamoyl chloride (1.0 μL, 0.0093 mmol) were added. When the reaction was complete as determined by HPLC-MS, the product was purified via preparative HPLC-MS (Waters SunFire C18, eluting with a gradient of MeCN/H2O containing 0.1% TFA). Yield: (6.3 mg, 90%).

Workup

  1. customthe product was purified via preparative HPLC-MS (Waters SunFire C18
  2. washeluting with a gradient of MeCN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-cdb6302878464e8eb1cdce4f0d02ef95
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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