Hydrochloric Acid → HCID 178481085, compound

HRID 39660Notes

Reaction equation

HRID 39660 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]2[NH:11][C:12]([C:14]3[N:15]([CH3:27])[CH:16]=[C:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:18]=3)=[N:13][C:8]2=[CH:7][CH:6]=1)=[O:4].Cl>[OH-].[Na+].O.O1CCOCC1>[C:23]([O:22][C:20]([NH:19][C:17]1[CH:18]=[C:14]([C:12]2[NH:11][C:9]3=[N:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[C:8]3[N:13]=2)[N:15]([CH3:27])[CH:16]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178497317HCID 178497317, compound

Product 1

HCID 178481085HCID 178481085, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Compound 8 (60 mg, 0.6 mmol) was dissolved in 0.2 M NaOH in H2O/dioxane 1:1 (7 mL) and stirred for 5 h at r.t. while the solution turned orange. The solution was cooled to 0° C. and 1N HCl was added dropwise until pH 1-2, while an orange precipitate developed. The product was separated by centrifugation, the supernatant removed, and the formed precipitate washed with cold H2O (2×2 mL). Lyophilization afforded 46 mg (81%) of 9 as an orange solid. Data of 9: UV (MeOH): λmax 359. 1H NMR (300 MHz, DMSO-d6): δ 1.46 (s, 9H), 4.05 (s, 3H), 7.01 (brs, 1H, D2O exchange), 7.15 (s, 1H), 7.98 (m, 3H), 9.30 (s, 1H, D2O exchange). 13C NMR (75 MHz, DMSO-d6): δ 28.96, 37.47, 79.21, 106.38, 118.65, 119.93, 120.44, 122.32, 124.99, 141.58, 150.32, 153.38, 166.53. MS (ESI): m/z (rel intensity) 358 (100). HRMS (FAB): m/z calcd for C17H20N5O4, 358.1515; found, 358.1506.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe product was separated by centrifugation
  3. customthe supernatant removed
  4. washthe formed precipitate washed with cold H2O (2×2 mL)

Sources & evidence

ORD record
ord-05b1bdd7c4d5480e924ae29e4514a813
Source dataset
uspto-grants-2013_09
Patent number
US08524899B2

Reaction notes

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