1-Hydroxybenzotriazole → HCID 178523386, compound

HRID 2042286Notes

Reaction equation

HRID 2042286 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:9][NH2:10])=[N:5][CH:6]=[CH:7][N:8]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.[CH2:42]([O:49][C:50]([NH:52][CH2:53][C@H:54]1[CH2:59][CH2:58][C@H:57]([C:60](O)=[O:61])[CH2:56][CH2:55]1)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)Cl>[Cl:2][C:3]1[C:4]([CH2:9][NH:10][C:60]([C@H:57]2[CH2:56][CH2:55][C@H:54]([CH2:53][NH:52][C:50](=[O:51])[O:49][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:59][CH2:58]2)=[O:61])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochlorideHCID 178523389HCID 178523389, compound

Product 1

HCID 178523386HCID 178523386, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of C-(3-chloropyrazin-2-yl)methylamine hydrochloride salt (0.100 g, 0.533 mmol) in DCM (1.35 mL) was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.16 g, 0.83 mmol), N,N-diisopropylethylamine (0.14 mL, 0.83 mmol), 1-hydroxybenzotriazole (0.075 g, 0.56 mmol) and trans-4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexanecarboxylic acid (0.21 g, 0.70 mmol). The reaction was stirred at rt overnight then diluted with DCM, washed with sat. NaHCO3 (aq) and brine, then dried over Na2SO4 and the solvent removed in vacuo. The residue thus isolated was chromatographed over silica gel eluting with EtOAc/hexane (1:1) to afford 0.173 g of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.00-1.03 (m, 2H), 1.45-1.51 (m, 2H), 1.83-1.89 (m, 2H), 1.99-2.03 (m, 2H), 2.20 (m, 1H), 3.05-3.12 (m, 3H), 4.68 (d, J=4.4 Hz, 2H), 4.79 (br, 1H), 5.10 (s, 2H), 6.79 (br, 1H), 7.31-7.37 (m, 5H), 8.33 (d, J=2.8 Hz, 1H), 8.46 (d, J=2.8 Hz, 1H). MS (ES+): m/z 417.14 [MH+].

Workup

  1. washwashed with sat. NaHCO3 (aq) and brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe residue thus isolated
  5. customwas chromatographed over silica gel eluting with EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-a92be8d8e8cd4dcfb5a18e31162c6c6e
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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