Hydrochloric Acid → HCID 69000525, compound

HRID 1909763Notes

Reaction equation

HRID 1909763 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3([C:31]#[N:32])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:33].CCOCC>O1CCOCC1>[ClH:33].[NH:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3([C:31]#[N:32])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69002504HCID 69002504, compound

Product 1

HCID 69000525HCID 69000525, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of the product from step 2 (30 mg, 0.07 mmol) in dioxane (1 mL) was added HCl (4 N in dioxane, 1 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 16 h. The solvent was reduced to 0.5 mL and ether (10 mL) was added to this vial. The resulting solid was filtered out and dried under vacuo to yield the title product, (17 mg, 85%); LCMS; 90%, ESI+ Calcd: 334.4, found m/z: 335.7 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 1.41-1.44 (m, 2H), 1.64-1.68 (m, 3H), 1.86-1.95 (m, 1H), 2.05-2.37 (m, 4H), 3.98-4.15 (m, 2H), 4.30-4.35 (m, 1H), 6.90-6.93 (m, 2H), 6.98-7.04 (m, 4H), 7.29-7.36 (m, 2H)

Workup

  1. additionwas added to this vial
  2. filtrationThe resulting solid was filtered out
  3. customdried under vacuo

Sources & evidence

ORD record
ord-e684d9ee74ac418f85828bf1f6f3161b
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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