Hydrochloric Acid → HCID 60198850, compound

HRID 2279582Notes

Reaction equation

HRID 2279582 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][CH:3]=1.Cl.O1CCOCC1>CO.C(Cl)Cl>[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][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68294380HCID 68294380, compound

Product 1

HCID 60198850HCID 60198850, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution 322 (28 mg, 0.056 mmol) in MeOH (2 mL) was added 4M HCl in dioxane (0.6 mL, 2.4 mmol) and the reaction stirred at RT 4 h. The reaction was diluted with DCM (25 mL) and satd. aq. NaHCO3 (25 mL), the phases separated and the aqueous phase extracted with 10% MeOH/DCM (25 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC plate (0.5 mm) developed with MeOH/DCM/NH4OH (9/90/1) to afford 6 mg (25%) of I-113 as a pale yellow residue: 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 0.6H), 8.02 (s, 0.4H), 7.15-7.30 (m, 4H), 4.80 (m, 1H), 4.52 (s, 1H), 4.34 (m, 1H), 4.09 (m, 1H), 3.74 (m, 1H), 3.59 (m, 1H), 3.47 (m, 1H), 2.79-2.92 (m, 3H), 2.51-2.73 (m, 3H), 2.42 (s, 1.2H), 2.39 (s, 2.8H), 1.87 (br s, 2H), 1.22 (m, 6H); LRMS (M+H) (APCI pos) m/e=402.1.

Workup

  1. customaq. NaHCO3 (25 mL), the phases separated
  2. extractionthe aqueous phase extracted with 10% MeOH/DCM (25 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on a preparative SiO2 TLC plate (0.5 mm)
  7. customto afford 6 mg (25%) of I-113 as a pale yellow residue

Sources & evidence

ORD record
ord-31f83e24904e47179c82565223dc2d02
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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