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

HRID 1809772Notes

Reaction equation

HRID 1809772 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]([NH:15][C:16]1[N:21]=[C:20]([C:22]2[C:30]3[C:25](=[N:26][C:27]([NH:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[N:28][CH:29]=3)[NH:24][N:23]=2)[CH:19]=[CH:18][N:17]=1)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)(C)(C)C.Cl>CCO>[N:34]1([CH2:33][CH2:32][NH:31][C:27]2[N:26]=[C:25]3[NH:24][N:23]=[C:22]([C:20]4[CH:19]=[CH:18][N:17]=[C:16]([NH:15][CH:9]([C:10]5[CH:14]=[CH:13][S:12][CH:11]=5)[CH2:8][NH2:7])[N:21]=4)[C:30]3=[CH:29][N:28]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178453679HCID 178453679, compound

Product 1

HCID 178511335N1-{4-[6-(2-morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2-{4-[6-(2-Morpholin-4-yl-ethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester (200 mg, 0.35 mmol) was dissolved in EtOH (4 mL), then conc. HCl (4 mL) was added. The reaction mixture was stirred at room temperature for 15 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-thiophen-3-yl-ethane-1,2-diamine; hydrochloride. (Yield 17 mg, 8.4%).

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-841c079158f242cc9cd145eed6bec8cf
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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