Water → HCID 69020964, compound

HRID 1007300Notes

Reaction equation

HRID 1007300 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:20][C:21]1[N:30]=[C:29]([NH:31][C@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:46][CH3:47])[CH:27]=2)[N:22]=1.O>C(Cl)Cl>[C:42]([O:41][C:39]([NH:38][C@@H:33]1[CH2:34][CH2:35][CH2:36][CH2:37][C@@H:32]1[NH:31][C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:46][CH3:47])[CH:27]=2)[N:22]=[C:21]([NH:20][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:30]=1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 69022112HCID 69022112, compound

Product 1

HCID 69020964HCID 69020964, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 68 mg of 4-chlorobenzoyl chloride and 200 mg of diisopropylethylamine in 8 mL of methylene chloride was combined with 150 mg of cis-2-(2-amino-6-methoxyquinazolin-4-yl)amino-N-tert-butoxycarbonylcyclohexylamine, and stirred at room temperature for 15 hours. The reaction solution was combined with water, extracted with chloroform, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain 120 mg of the desirable compound.

Workup

  1. extractionextracted with chloroform
  2. customdried
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-33dd6162b3e24197897f07644c7ae3b2
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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