Diisopropylethylamine → HCID 5279914, compound

HRID 1394432Notes

Reaction equation

HRID 1394432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:9][NH:10][C:3]=12.Cl.[Br:17][C:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[C:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)(Cl)Cl>[Br:17][C:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[C:19]1[CH2:20][CH2:21][N:22]([C:12](=[O:14])[C:11]([C:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]3[NH:10][CH:9]=2)=[O:15])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride2×HCID 22476293HCID 22476293, compoundHCID 67046638HCID 67046638, compound

Product 1

HCID 5279914HCID 5279914, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-oxo-acetic acid (191 mg, 0.87 mmol), 4-(bromophenylmethylene)-piperidine hydrochloride salt (245 mg, 0.85 mmol) and diisopropylethylamine (440 mg, 3.4 mmol) in chloroform (10 mL) was added BOPCl (261 mg, 1.02 mmol). The reaction solution was stirred two days, treated with additional diisopropylethylamine (440 mg, 3.4 mmol) and BOPCl (130 mg, 0.50 mmol) and stirred three days. The reaction mixture was concentrated, dissolved into MeOH and purified by preparative HPLC to yield title compound shown (293 mg, 0.64 mmol, 75%) as a white solid.

Workup

  1. stirringstirred three days
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved into MeOH
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e85a2e6f8b9349018467fcfa31e56979
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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