Borane;tetrahydrofuran → HCID 86590029, compound

HRID 2415789Notes

Reaction equation

HRID 2415789 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]3[O:23][CH2:22][CH2:21][CH2:20][N:19]([CH2:24][C:25](O)=[O:26])[C:18]=3[CH:28]=1)=[O:12])=[CH:5]2.B.C1COCC1>C1COCC1>[OH:26][CH2:25][CH2:24][N:19]1[C:18]2[CH:28]=[C:14]([NH:13][C:11]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=4)=[O:12])[CH:15]=[CH:16][C:17]=2[O:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 22636752HCID 22636752, compound

Product 1

HCID 86590029HCID 86590029, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[(5-Chloro-1H-indole-2-carbonyl)-amino]-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl}-acetic acid (80 mg) was dissolved in THF (3 mL) and treated with 1.0 M BH3/THF at room temperature. The reaction was concentrated in vacuo, diluted with EtOAc and washed with 1N HCl. The crude product was purified by preparative TLC (EtOAc) to yield 27 mg of the product as a crystalline solid. LCMS: AP+ 386/388.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with 1N HCl
  4. customThe crude product was purified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-e4daaad55ec149ce85b6ff02bdfe7839
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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