Triethylamine → HCID 65573179, compound

HRID 1692373Notes

Reaction equation

HRID 1692373 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[N:43]1([CH:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)[CH2:47][CH2:46][CH2:45][CH2:44]1>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:5]([N:51]2[CH2:52][CH2:53][CH:48]([N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)[CH2:49][CH2:50]2)=[O:7])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 787034-(1-Pyrrolidinyl)piperidineHCID 27355903-Bromo-2-methylbenzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 65573179HCID 65573179, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.22 g (1.0 mmol) of 3-bromo-2-methyl-benzoic acid was dissolved in 10 ml of DMF and the solution was treated with 0.38 g (1.0 mmol) of HATU. Then, 0.42 ml=0.30 g (3.0 mmol) of Et3N was added and after 30 min, a solution of 0.16 g (1.0 mmol) of 4-pyrrolidin-1-yl-piperidine in 5 ml of DMF. After 3 hours, the reaction mixture was poured into crashed ice and extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.33 g (95%) of the title compound as light red solid. MS: 351.2 (MH+, 1 Br).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted three times with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

Sources & evidence

ORD record
ord-159c08b7c2564f6f87610ecabcf160ce
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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