Hydrochloric Acid → HCID 58546840, compound

HRID 1850322Notes

Reaction equation

HRID 1850322 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([N:21]3[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.Cl.C(OCC)C>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH:13]([C:15]2[C:16]([N:21]3[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:14]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58547629HCID 58547629, compound

Product 1

HCID 58546840HCID 58546840, compoundYield 68.3%

Procedure

To a round bottomed flask was added tert-butyl (1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-yl)carbamate (1.3145 g, 2.94 mmol) and hydrogen chloride, 1M in diethyl ether (0.089 ml, 2.94 mmol) to stir. Solvent was evaporated. The reaction mixture was diluted with saturated sodium bicarbonate and extracted with CH2Cl2. The organic extract was washed with water, saturated Na2CO3, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo to give 1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-amine (0.696 g, 2.009 mmol, 68.2% yield).

Workup

  1. customSolvent was evaporated
  2. additionThe reaction mixture was diluted with saturated sodium bicarbonate
  3. extractionextracted with CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with water, saturated Na2CO3, saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a357d926572c4c3b87c161dc8e3e37f3
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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