Hydrochloric Acid → HCID 67305646, compound

HRID 1921976Notes

Reaction equation

HRID 1921976 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([NH:21][CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=3)[CH:6]=[CH:5][N:4]=1.[ClH:36].C(OCC)C>O1CCOCC1>[ClH:36].[CH3:20][O:19][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:18]=[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([N:2]([CH3:35])[CH3:1])[N:8]=1)[CH:10]=[C:11]2[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67305284Tert-butyl 4-((3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)amino)piperidine-1-carboxylate

Product 1

HCID 67305646HCID 67305646, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-((3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)amino)piperidine-1-carboxylate (142) (215 mg, 0.45 mmol) in dioxane (6 ml) was added 4 M hydrochloric acid in dioxane (3 ml). The mixture was stirred at room temperature for 24 hours. Diethylether (100 ml) was added and the solid isolated by centrifugation. The solid was washed with diethylether (2×50 ml) and dried under vacuum to give 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) as a pale yellow/orange solid (196 mg). LCMS m/e 378 (M+H)

Workup

  1. customthe solid isolated by centrifugation
  2. washThe solid was washed with diethylether (2×50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0da7e3a4b4234470906cd210ca316d9a
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

Loading…