1-Hydroxybenzotriazole → HCID 10141615, compound

HRID 900744Notes

Reaction equation

HRID 900744 reaction equation
ON1C2C=CC=CC=2N=N1.[CH3:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([C:35](O)=[O:36])=[C:20]([CH2:22][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[C:24]3[CH2:32][CH2:33][CH3:34])[S:21][C:15]=2[N:14]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:13]1=[O:42].Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:56][NH:57][O:58][CH3:59]>ClCCl.C(N(CC)CC)C>[CH3:59][O:58][N:57]([CH3:56])[C:35]([C:19]1[C:16]2[C:17](=[O:18])[N:12]([CH3:11])[C:13](=[O:42])[N:14]([CH2:38][CH:39]([CH3:40])[CH3:41])[C:15]=2[S:21][C:20]=1[CH2:22][N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[CH2:32][CH2:33][CH3:34])=[O:36]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68807167HCID 68807167, compound

Product 1

HCID 10141615HCID 10141615, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-Hydroxybenzotriazole (0.14 g) was added to a solution of the product of step b) (0.25 g) in dichloromethane (5 ml). After stirring for 5 minutes, 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide hydrochloride (0.21 g) was added. After stirring for 10 minutes, N,O-dimethylhydroxylamine hydrochloride (0.1 g) and triethylamine (0.15 ml) were added The reaction mixture was stirred for 12 h at room temperature. The solution was concentrated in vacuo. The residue was purified by flash silica chromatography eluting with a gradient of 0-3% methanol in dichloromethane to give the title compound as a yellow solid (0.118 g).

Workup

  1. stirringAfter stirring for 10 minutes
  2. stirringwas stirred for 12 h at room temperature
  3. concentrationThe solution was concentrated in vacuo
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with a gradient of 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-1d731b16c4e544d79a85ec6b1d6264f3
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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