1-Hydroxybenzotriazole → HCID 178523386, compound

HRID 2076501Notes

Reaction equation

HRID 2076501 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-e62c4fe4303d4f0998e9b9b3ed0ca69c
Source dataset
uspto-grants-2011_04
Patent number
US07923555B2

Reaction notes

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