Tryptamine → HCID 68165064, compound

HRID 921287Notes

Reaction equation

HRID 921287 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([P:19]([CH3:22])([CH3:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.C(N(CC)CC)C.[NH2:30][CH2:31][CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1>C(O)C>[CH3:21][P:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:30][CH2:31][CH2:32][C:33]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[NH:35][CH:34]=3)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)([CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 86668788HCID 86668788, compound

Product 1

HCID 68165064HCID 68165064, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine (prepared as in Example 1: 40 mg, 0.12 mmol) in 2 mL of ethanol was added 50 L of triethylamine and Tryptamine (18 mg, 0.12 mmol). The mixture was microwave at 120 degrees for 20 minutes. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield a white solid as product (44 mg, 81% yield.) MS/ES+: m/z=474.

Workup

  1. customat 120 degrees
  2. customfor 20 minutes
  3. filtrationThe reaction mixture was filtered through a syringe
  4. filtrationfilter
  5. custompurified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases)
  6. customto yield a white solid as product (44 mg, 81% yield.) MS/ES+

Sources & evidence

ORD record
ord-eca55b70c5bc46d0ae842cec32f5c37a
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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