Hydrochloric Acid → HCID 60198466, compound

HRID 2279465Notes

Reaction equation

HRID 2279465 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:19][C:20]([N:22]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][C:26]([NH:32][CH:33]([CH3:35])[CH3:34])=[N:25][C:24]=3[CH2:23]2)=[O:21])[CH2:9][N:10](C)[C:11](=O)OC(C)(C)C)=[CH:4][C:3]=1[F:36].C(Cl)Cl.Cl.O1CCOCC1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:9][NH:10][CH3:11])[CH2:19][C:20]([N:22]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][C:26]([NH:32][CH:33]([CH3:35])[CH3:34])=[N:25][C:24]=3[CH2:23]2)=[O:21])=[CH:4][C:3]=1[F:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 86705480HCID 86705480, compound

Product 1

HCID 60198466HCID 60198466, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 106 (106 mg, 0.204 mmol) in MeOH (2 mL) and a small amount of DCM was added 4 M HCl in dioxane (764 μL, 3.06 mmol). The reaction was stirred at RT for 4 h. The reaction was concentrated and purified by reverse phase column chromatography (SP4) eluting with a MeCN/H2O gradient (0-80% MeCN) to afford 50.7 mg (54.5%) of I-17: LCMS (ACPI-pos) m/z 420.3 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reverse phase column chromatography (SP4)
  3. washeluting with a MeCN/H2O gradient (0-80% MeCN)
  4. customto afford 50.7 mg (54.5%) of I-17

Sources & evidence

ORD record
ord-86d5169459024d9e96b36596c6eaccf7
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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