Pyridine → HCID 86636480, compound

HRID 1666603Notes

Reaction equation

HRID 1666603 reaction equation
[ClH:1].Cl.[C:3]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]2[N:27]=[C:26]([N:28]3[CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH2:13]1)=[O:11].N1C=CC=CC=1.[C:47](OC(=O)C)(=[O:49])[CH3:48]>C(Cl)(Cl)Cl>[ClH:1].[C:47]([N:31]1[CH2:32][CH2:33][CH2:34][N:28]([C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]([NH:17][C@H:14]3[CH2:15][CH2:16][N:12]([C:10](=[O:11])[CH2:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:13]3)[N:27]=2)[CH2:29][CH2:30]1)(=[O:49])[CH3:48]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67444177HCID 67444177, compound

Product 1

HCID 86636480HCID 86636480, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-Butyl 4-(2-((S)-1-(2-biphenyl-2-ylethanoyl)pyrrolidin-3-ylamino)quinazolin-4-yl)-[1,4]diazepane-1-carboxylate (0.53 g) synthesized in the same manner as in Example 1 was dissolved in ethyl acetate (3 mL), followed by addition of a solution (2.2 mL) of 4 M HCl in ethyl acetate, and the mixture was stirred overnight. Precipitated solids were collected by filtration and then washed with hexane to obtain 2-biphenyl-2-yl-1-((S)-3-(4-[1,4]diazepan-1-ylquinazolin-2-ylamino)pyrrolidin-1-yl)ethanone dihydrochloride (0.15 g). (2) 2-Biphenyl-2-yl-1-((S)-3-(4-[1,4]diazepan-1-ylquinazolin-2-ylamino)pyrrolidin-1-yl)ethanone di hydrochloride (40 mg) was suspended in chloroform (3 mL), followed by addition of pyridine (12 mg) and acetic anhydride (8.5 mg), and the mixture was stirred at room temperature for 3 h. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (chloroform/methanol=10:1) to obtain the title compound (compound 1-210) (46 mg). The resulting purification product was dissolved in ethyl acetate (1.0 mL), followed by addition of a solution (0.015 mL) of 4 M HCl in ethyl acetate, and the mixture was stirred to obtain the title compound (compound 1-212) (12 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography (chloroform/methanol=10:1)

Sources & evidence

ORD record
ord-705d049aa93b4c06ad13951f2fe7b12c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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