6-Bromo-2-chloroquinazoline → tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate

HRID 56359Notes

Reaction equation

HRID 56359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[N:6]=[CH:5]2.[NH2:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 179135596-Bromo-2-chloroquinazolineHCID 45091940tert-butyl N-[(1S,2R)-2-aminocyclopentyl]carbamate

Product 1

HCID 118043383tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamateYield 59.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-2-chloroquinazoline (1 g, 4.14 mmol) and tert-butyl ((1S,2R)-2-aminocyclopentyl)carbamate (0.826 g, 4.14 mmol) were stirred at 100° C. in Dioxane (10 mL) for 48 h. The reaction mixture was cooled to room temperature, concentrated and the residue was purified by silica gel column chromatography to afford tert-butyl ((1S,2R)-2-((6-bromoquinazolin-2-yl)amino)cyclopentyl)carbamate (1 g, 59%). MS (ES+) C18H23BrN4O2 requires: 406, found: 407 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b40b4d7550840f3bf24ad3cf88aaad8
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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