Hydrochloric Acid → (1R,2S)-N1-(6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)cyclopentane-1,2-diamine

HRID 56361Notes

Reaction equation

HRID 56361 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([NH:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[NH:28]C(=O)OC(C)(C)C)[N:16]=[CH:15]2.Cl>O1CCOCC1.ClCCl>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([NH:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[NH2:28])[N:16]=[CH:15]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118043384tert-butyl ((1S,2R)-2-((6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate

Product 1

HCID 118036396(1R,2S)-N1-(6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)cyclopentane-1,2-diamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl ((1S,2R)-2-((6-(2-chloro-3-ethoxy-6-fluorophenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate (51 mg, 0.1 mmol) and 4M HCl in Dioxane (0.5 mL) in dichloromethane (1 mL) was stirred at room temperature for 2 h. LC-MS indicated complete consumption of SM. The reaction mixture was concentrated and used without further purification in the next step.

Workup

  1. customconsumption of SM
  2. concentrationThe reaction mixture was concentrated
  3. customused without further purification in the next step

Sources & evidence

ORD record
ord-882b78db619a4615bb35d9faedc0020e
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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