Veratrylamine → HCID 67496265, compound

HRID 1022476Notes

Reaction equation

HRID 1022476 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:18]([NH2:29])[C:19]1[CH:28]=[CH:27][C:24]([O:25][CH3:26])=[C:21]([O:22][CH3:23])[CH:20]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:6]([CH:10]=1)[C:7]([NH:29][CH2:18][C:19]1[CH:28]=[CH:27][C:24]([O:25][CH3:26])=[C:21]([O:22][CH3:23])[CH:20]=1)=[O:9]

Participants

6

Reactant 4

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67496094HCID 67496094, compound

Product 1

HCID 67496265HCID 67496265, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 g of the compound obtained in Step 1.1, 0.646 g of veratrylamine, 1.152 g of DIEA and 1.69 g of HBTU in 50 ml of DMF is stirred for 2 days at room temperature. The reaction medium is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (100/0, v/v) to (80/20, v/v) to give 1.2 g of a solid, which is used without purification in the following step.

Workup

  1. customThe reaction medium is evaporated under reduced pressure
  2. customThe residue is chromatographed on silica gel
  3. washeluting with a DCM/EtOAc mixture from (100/0

Sources & evidence

ORD record
ord-8ac093f5953740af86c1fa03d2722a97
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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