Methanol → HCID 178457879, compound

HRID 2117269Notes

Reaction equation

HRID 2117269 reaction equation
[O:1]=[C:2]1[C:8](=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[C:7](=[O:19])[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=[CH:4][N:3]1[CH2:26][C:27]([N:29]([CH:38]([CH3:40])[CH3:39])[C:30]1[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=1)=[O:28].B(Br)(Br)Br.CO>ClCCl>[O:1]=[C:2]1[C:8](=[CH:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[C:7](=[O:19])[N:6]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[CH:4][N:3]1[CH2:26][C:27]([N:29]([C:30]1[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=1)[CH:38]([CH3:40])[CH3:39])=[O:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 178492377HCID 178492377, compound

Product 1

HCID 178457879HCID 178457879, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 2-[2,4-dioxo-3-(1H-indazol-3-ylmethylene)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (Example 1) (1 g, 1.86 mM) in 50 ml of dichloromethane was cooled to 0° C. and 10 fold excess of BBr3 was added. The reaction mixture was stirred for 3 hrs at room temp., cooled to 0° C. and methanol was added dropwise. Organic solvents were evaporated under reduced pressure and residue was purified using column chromatography on silica gel using mixture of Hexane-Ethyl Acetate (1:3) as an eluent providing 700 mg of pure racemic product.

Workup

  1. customOrganic solvents were evaporated under reduced pressure and residue
  2. customwas purified
  3. additionon silica gel using mixture of Hexane-Ethyl Acetate (1:3) as an eluent

Sources & evidence

ORD record
ord-5f7d329e4b4b41078bbc582890753b99
Source dataset
uspto-grants-2008_10
Patent number
US07442693B2

Reaction notes

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