Diisopropylethylamine → HCID 59369701, compound

HRID 45400

Reaction equation

HRID 45400 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[C:5]([CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[N:6]=1.C(N(C(C)C)CC)(C)C.[CH2:32]([C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1>ClCCl.C(OCC)(=O)C>[CH2:16]([NH:15][C:13]([C:4]1[S:3][C:2]([NH:1][C:43](=[O:44])[C:42]2[CH:41]=[CH:40][C:39]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:47][CH:46]=2)=[N:6][C:5]=1[CH2:7][N:8]([CH2:9][CH3:10])[CH2:11][CH3:12])=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1364294-Benzylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866425252-amino-N-benzyl-4-((diethylamino)methyl)thiazole-5-carboxamide

Product 1

HCID 59369701HCID 59369701, compoundYield 3.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-N-benzyl-4-((diethylamino)methyl)thiazole-5-carboxamide (0.052 g, 0.16 mmol) and diisopropylethylamine (0.30 mL, 1.70 mmol) in dichloromethane (5 mL) was added 4-benzylbenzoic acid (0.046 g, 0.21 mmol) followed by the addition of N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.076 g, 0.20 mmol). The reaction mixture was stirred at ambient temperature for 18 h, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by preparative HPLC (acetone/water gradient) to afford the title compound (0.003 g); MS (ES+) m/z 513.

Workup

  1. washwashed with saturated sodium bicarbonate solution, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by preparative HPLC (acetone/water gradient)

Sources & evidence

ORD record
ord-2767760b1be14db685a7ea992c725540
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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