Diisopropylethylamine → HCID 59406925, compound

HRID 1948309Notes

Reaction equation

HRID 1948309 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([OH:11])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[NH2:56][C@H:57]1[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:59][C@H:58]1[O:68][CH3:69]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:56][C@H:57]1[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][CH3:67])=[O:64])[CH2:59][C@H:58]1[O:68][CH3:69])=[O:11]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 251376823,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid2×HCID 131730313HCID 131730313, compound2×

Product 1

HCID 59406925HCID 59406925, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 1; 304 mg) was dissolved in anhydrous DMF. HATU (596 mg), HOAT (213 mg) and DIEA (274 μl) were added and stirred at ambient for 15 min. Cis(±)ethyl 4-amino-3-methoxypiperidine-1-carboxylate (Intermediate 21; 317 mg) was added and the mixture was stirred at ambient for 18 h. The mixture was diluted with EtOAc and washed with water, 1N HCl, bicarbonate buffer, water, brine and dried over Na2SO4. The solution was concentrated in vacuo to give the title compound as a brown solid (503 mg). MS (ES) MH+: 378, 380 for C15H21Cl2N3O4; NMR: 1.29 (t, 3H), 1.79 (m, 2H), 2.27 (s, 3H), 3.12 (m, 2H), 3.30 (s, 3H), 3.37 (m, 1H), 3.83-4.16 (m, 5H), 7.25 (d, 1H), 12.23 (s, 1H).

Workup

  1. stirringthe mixture was stirred at ambient for 18 h
  2. washwashed with water, 1N HCl, bicarbonate buffer, water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7feb247f6cce41e79cb12bee4fd27dcf
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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