Hydrochloric Acid → {1-[1-(4-Aminomethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester dihydrochloride

HRID 1040509Notes

Reaction equation

HRID 1040509 reaction equation
[ClH:1].[CH2:2]([O:9][C:10](=[O:36])[NH:11][C:12]1([C:15](=[O:35])[NH:16][C:17]2([C:20]3[CH:25]=[C:24]([CH2:26][NH:27]C(OC(C)(C)C)=O)[CH:23]=[CH:22][N:21]=3)[CH2:19][CH2:18]2)[CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[CH2:2]([O:9][C:10](=[O:36])[NH:11][C:12]1([C:15](=[O:35])[NH:16][C:17]2([C:20]3[CH:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[CH:22][N:21]=3)[CH2:18][CH2:19]2)[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67390574(1-{1-[4-(tert-Butoxycarbonylamino-methyl)-pyridin-2-yl]-cyclopropylcarbamoyl}-cyclopropyl)-carbamic acid benzyl ester

Product 1

HCID 67389523{1-[1-(4-Aminomethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl solution in 1,4-dioxane (15 mL) was added to (1-{1-[4-(tert-Butoxycarbonylamino-methyl)-pyridin-2-yl]-cyclopropylcarbamoyl}-cyclopropyl)-carbamic acid benzyl ester (1.403 g, 2.92 mmol). The resultant mixture was allowed to stir at RT for 6 h. The mixture was concentrated to afford a light brown solid. This solid was washed with diethyl ether and dried in vacuo to afford 1.271 g of {1-[1-(4-Aminomethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester di-hydrochloric acid salt.

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford a light brown solid
  3. washThis solid was washed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-46fc33ab8a1a45e9910eee6176e6513d
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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