1-Hydroxybenzotriazole → HCID 86699107, compound

HRID 1424195Notes

Reaction equation

HRID 1424195 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[Br:40][C:41]1[CH:42]=[C:43]([NH2:48])[C:44]([NH2:47])=[CH:45][CH:46]=1>C(Cl)Cl.O>[NH2:47][C:44]1[CH:45]=[CH:46][C:41]([Br:40])=[CH:42][C:43]=1[NH:48][C:14](=[O:16])[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:13])[CH3:17]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 3235934-Bromobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86699107HCID 86699107, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[(benzyloxy)carbonyl]-2-methylalanine (Preparation 56, 35 g, 0.15 mmol) in DCM (600 mL) was added HOBt (25 g, 0.18 mmol) followed by EDCI.HCl (35.5 g, 0.18 mmol) and the reaction stirred at room temperature for 30 minutes. 4-Bromobenzene-1,2-diamine (30.7 g, 0.16 mmol) was added and the reaction heated to reflux for 24 hours. The reaction was cooled and poured into water (500 mL). The organic layer was separated, washed with water (200 mL), brine (100 mL) dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography to afford the title compound as a brown solid that was taken directly on to the next step (80 g, 66%).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction was cooled
  4. customThe organic layer was separated
  5. washwashed with water (200 mL), brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-9f4bfd58b2254b318dbe11d96ded26ff
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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