Veratrylamine → HCID 67496232, compound

HRID 1022477Notes

Reaction equation

HRID 1022477 reaction equation
[I: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.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:51]([NH2:62])[C:52]1[CH:61]=[CH:60][C:57]([O:58][CH3:59])=[C:54]([O:55][CH3:56])[CH:53]=1>CN(C=O)C>[CH3:56][O:55][C:54]1[CH:53]=[C:52]([CH:61]=[CH:60][C:57]=1[O:58][CH3:59])[CH2:51][NH:62][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[NH:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67496151HCID 67496151, compound

Product 1

HCID 67496232HCID 67496232, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.22 g of 5-iodo-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acid, 18.4 g of HBTU, 21.28 g of DIEA and 9.18 g of veratrylamine in 200 ml of DMF is stirred overnight at room temperature. The reaction medium is evaporated under reduced pressure. The residue is taken up in 3000 mL of EtOAc. The solution is washed with aqueous 0.5N HCl solution, with saturated aqueous NaHCO3 solution, and then with saturated aqueous NaCl solution. The organic phase is dried over MgSO4, filtered and evaporated under reduced pressure to give 18 g of the expected product.

Workup

  1. customThe reaction medium is evaporated under reduced pressure
  2. washThe solution is washed with aqueous 0.5N HCl solution, with saturated aqueous NaHCO3 solution
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-594df479e3474eac992c167d5125935d
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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