Hydrochloric Acid → N4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(1-methylimidazol-4-yl)pyrimidine-2,4-diamine hydrochloride

HRID 1478048Notes

Reaction equation

HRID 1478048 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:33][CH2:32][C:19]3([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[N:10]=[CH:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.Cl>C(Cl)Cl.CCOC(C)=O>[ClH:1].[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:33][CH2:32][C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[N:10]=[CH:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118389996tert-butyl 9-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 118390036N4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(1-methylimidazol-4-yl)pyrimidine-2,4-diamine hydrochlorideYield 197.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 9-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (292 mg, 0.6134 mmol) in DCM (10 mL) was added a solution of HCl in EtOAc (8 mL, 3 mol/L). The reaction was stirred overnight at rt and concentrated in vacuo to give the title compound as a yellow solid (250 mg, 98.82%).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f13810cd7264a0397a2156392c9452b
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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