Diisopropylethylamine → HCID 86643332, compound

HRID 1948289Notes

Reaction equation

HRID 1948289 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23](O)=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:26][CH3:27])=[O:10].CN([C:31]([O:35][N:36]1N=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.CON>CC(N(C)C)=O.CCOC(C)=O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([NH:36][O:35][CH3:31])=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:26][CH3:27])=[O:10]

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 181649HOAtHCID 521874O-Methylhydroxylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86643333HCID 86643333, compound

Product 1

HCID 86643332HCID 86643332, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

Cis(±)2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2 -yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acid (Example 35; 100 mg) was dissolved in anhydrous DMA (2 ml). HATU (97 mg), HOAT (31 mg), DIEA (41 μl) were added and the mixture was stirred for 30 min. N-Methoxyamine hydrochloride (19.3 mg) was added followed by DIEA (41 μl), and the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc, washed with H2O, 20% citric acid solution, H2O, sat. NaHCO3, H2O, brine and dried over Na2SO4. The organic phase was concentrated in vacuo to give the title compound as an off-white solid (82 mg). MS (ES)(MH+): 462, 460 for C17H21Cl2N5O4S; NMR: 1.64 (m, 2H), 1.85 (m, 1H), 2.05 (s, 3H), 2.83 (m, 1H), 3.33 (m, 5H), 3.73 (s, 3H), 4.07 (m, 1H), 4.38 (m, 2H), 7.24 (d, 1H), 7.74 (s, 1H), 11.39 (s, 1H), 12.05 (s, 1H).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. washwashed with H2O, 20% citric acid solution, H2O, sat. NaHCO3, H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-c39450f364ba4e2f8df44d24f0ce79a5
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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