1-Hydroxybenzotriazole → HCID 57874446, compound

HRID 1093706Notes

Reaction equation

HRID 1093706 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13](=[O:18])[CH2:14][C:15]([OH:17])=O)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[Cl:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][CH:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1>CN(C=O)C.O>[Cl:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][CH:60]1[CH2:65][CH2:64][N:63]([C:15](=[O:17])[CH2:14][C:13]([NH:12][C:10]2[S:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][N:9]=2)=[O:18])[CH2:62][CH2:61]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874410HCID 57874410, compoundHCID 66591362HCID 66591362, compound

Product 1

HCID 57874446HCID 57874446, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(5-phenyl-thiazol-2-yl)-malonamic acid (0.075 g, 0.00028 mole) in DMF (2 mL) was added DIPEA (0.11 g, 0.00085 mole), HOBt (0.038 g, 0.00028 mole) and EDCI.HCl (0.065 g, 0.00034 mol). After 2 minutes (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (0.077 g, 0.00031 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and hexane to afford 0.035 g (28%) of 3-[4-(2-chloro-phenylamino)-piperidin-1-yl]-3-oxo-N-(5-phenyl-thiazol-2-yl)-propionamide. LC-MS purity: 455.11 (M+1)+, 98.03%, 1H NMR (CDCl3): δ 11.6 (s, 1H), 7.9 (d, 2H), 7.4 (t, 3H), 7.3 (t, 2H), 7.2 (m, 2H), 7.1, 6.70 (m, 2H), 4.5 (d, 1H), 4.2 (d, 1H), 3.9 (d, 1H), 3.6 (s, 3H), 3.3 (t, 1H), 3.1 (t, 1H), 2.2 (s, 2H), 1.5 (m, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a21f3a8935d843bbb0e5e3f8ea946e8c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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