Hydrochloric Acid → N1-{4-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine

HRID 1809770Notes

Reaction equation

HRID 1809770 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]([NH:17][C:18]1[N:23]=[C:22]([C:24]2[C:32]3[C:27](=[N:28][C:29]([NH:33][CH2:34][CH2:35][N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[N:30][CH:31]=3)[NH:26][N:25]=2)[CH:21]=[CH:20][N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.Cl>CCO>[N:36]1([CH2:35][CH2:34][NH:33][C:29]2[N:28]=[C:27]3[NH:26][N:25]=[C:24]([C:22]4[CH:21]=[CH:20][N:19]=[C:18]([NH:17][CH:10]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH2:9][CH2:8][NH2:7])[N:23]=4)[C:32]3=[CH:31][N:30]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178453508HCID 178453508, compound

Product 1

HCID 178511122N1-{4-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3-{4-[6-(2-Morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester (150 mg, 0.26 mmol) was dissolved in EtOH (4 mL), then conc. HCl (4 mL) was added. The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure to afford the crude product which was purified by prep-HPLC to afford N1-{4-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine; hydrochloride. (Yield 30 mg, 19.5%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford the crude product which
  3. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-f3533fc8942d49ccbfee1afe54512a77
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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