Hydrochloric Acid → HCID 58299574, compound

HRID 875992Notes

Reaction equation

HRID 875992 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[N:38][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[K+].[K+].Cl>ClCCl.O1CCOCC1.C(OCC)C.C(OCC)(=O)C.CO>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[N:38][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58299569HCID 58299569, compound

Product 1

HCID 58299574HCID 58299574, compoundYield 84%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Compound 269 (120 mg, 220 μmol) was dissolved in dichloromethane (4 mL). Trifluoroacetic acid (0.400 mL, 2203 μmol) was added and the reaction stirred at room temperature for 70 minutes. The reaction was added to aqueous K2CO3 (10%, 30 mL) and extracted thrice with dichloromethane. The combined organics were dried (MgSO4) and evaporated to give a pale yellow solid, 82 mg. This residue was dissolved in dioxane (2 mL) and methanol (2 mL) and 1 mL of a saturated solution of HCl in dioxane was added. ethyl acetate (30 mL) followed by diethyl ether (30 mL) were added to precipitate the HCl salt, which was collected and dried in vacuo to give compound 266 as a yellow solid (77 mg, 84%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.24-9.36 (m, 4 H) 9.19 (s, 1 H) 8.52 (s, 1 H) 7.97 (s, 1 H) 7.92-7.96 (m, 1 H) 7.44-7.54 (m, 1 H) 6.83 (d, J=8.56 Hz, 1 H) 5.31-5.43 (m, 1 H) 3.94 (s, 3 H) 3.33-3.41 (m, 4 H) 3.21 (br. s., 4 H) 1.95-2.11 (m, 4 H) 1.70 (none, 2 H) ppm.

Workup

  1. extractionextracted thrice with dichloromethane
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a pale yellow solid, 82 mg
  5. additionwere added
  6. customto precipitate the HCl salt, which
  7. customwas collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d99196d8bd4c487f82767573e6a09a0d
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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