Hydrochloric Acid → HCID 178479284, compound

HRID 707283Notes

Reaction equation

HRID 707283 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[N:14]([CH:21]3[CH2:23][CH2:22]3)[C:13]2=[O:24])[CH2:9]1)(C)(C)C.[ClH:26].O1CCOCC1>CO>[ClH:26].[NH2:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[N:14]([CH:21]3[CH2:22][CH2:23]3)[C:13]2=[O:24])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178454108HCID 178454108, compound

Product 1

HCID 178479284HCID 178479284, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottomed flask was added tert-butyl(trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)carbamate (1.905 g, 5.52 mmol) and hydrogen chloride, 4.0M solution in 1,4-dioxane (1.915 ml, 55.2 mmol) to stir at room temperature. The reaction was monitored by TLC until completion (10% MeOH/90% DCM). The reaction mixture was filtered and solids were washed with diethyl ether and dried in a vacuum oven to give the title compound (1.0201 g, 3.62 mmol, 65.6% yield). LCMS showed product peak at 0.997 min (m+1=246.1). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.94-1.06 (m, 4 H) 2.52-2.60 (m, 2 H) 2.90-2.99 (m, 1 H) 3.16 (ddd, J=14.52, 8.66, 7.34 Hz, 2 H) 3.96-4.08 (m, 1 H) 5.21-5.33 (m, 1 H) 7.92-8.01 (m, 2 H) 8.34 (br. s., 3 H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washsolids were washed with diethyl ether
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0089de6faea74e568da4ffb65d658eda
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…