Hydrochloric Acid → 4-(2-(((1R,2S)-2-aminocyclopentyl)amino)quinazolin-6-yl)-N-cyclopropyl-3-methoxybenzamide

HRID 56366Notes

Reaction equation

HRID 56366 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[C:18]([NH:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][C@@H:25]3[NH:29]C(=O)OC(C)(C)C)[N:17]=[CH:16]4)=[C:9]([O:37][CH3:38])[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.Cl>O1CCOCC1.ClCCl>[NH2:29][C@H:25]1[CH2:26][CH2:27][CH2:28][C@H:24]1[NH:23][C:18]1[N:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])=[CH:8][C:9]=3[O:37][CH3:38])[CH:14]=2)[N:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131736913tert-butyl ((1S,2R)-2-((6-(4-(cyclopropylcarbamoyl)-2-methoxyphenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate

Product 1

HCID 1180362304-(2-(((1R,2S)-2-aminocyclopentyl)amino)quinazolin-6-yl)-N-cyclopropyl-3-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl ((1S,2R)-2-((6-(4-(cyclopropylcarbamoyl)-2-methoxyphenyl)quinazolin-2-yl)amino)cyclopentyl)carbamate (58 mg, 0.11 mmol) and 4M HCl in Dioxane (0.8 mL) in dichloromethane (1.5 mL) was stirred at room temperature for 120 minutes. 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-541b657c4e49474ea4fff2bba1d973ea
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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