Hydrochloric Acid → HCID 86696272, compound

HRID 2175149Notes

Reaction equation

HRID 2175149 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[N:17][C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([S:25][C:26]2[N:30]4[CH:31]=[C:32]([C:35]([O:37]CC)=[CH2:36])[CH:33]=[CH:34][C:29]4=[N:28][N:27]=2)=[CH:20][CH:19]=3)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl>C1COCC1>[OH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[N:17][C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([S:25][C:26]2[N:30]4[CH:31]=[C:32]([C:35](=[O:37])[CH3:36])[CH:33]=[CH:34][C:29]4=[N:28][N:27]=2)=[CH:20][CH:19]=3)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86696270HCID 86696270, compound

Product 1

HCID 86696272HCID 86696272, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (76.2) (90 mg, 0.160 mmol) in THF (2 ml) was added about 2 N HCl (1 mL) at rt and the mixture was continue stirred for 30 mins, Checked the reaction by LCMS and TLC. The reaction solution was neutralized with sat.NaHCO3 aqueous until the pH to 8˜9 and extracted with DCM for three times, the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give crude product which was purified by flash chromatography and eluented with DCM/MeOH (40:1˜20:1) to obtained pure desired product (76.3) as yellow solid (42 mg, yield 62.5%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.95 (s, 1H), 8.72 (s, 1H), 7.98 (d, 1H), 7.87 (d, 1H), 7.80 (d, 1H), 7.75 (s, 1H), 7.39-7.43 (m, 2H), 3.78-3.84 (m, 1H), 3.68-3.74 (m, 2H), 3.02-3.08 (m, 2H), 2.57 (s, 3H), 1.98-2.01 (m, 2H), 1.62-1.71 (m, 2H). LCMS (method A): [M+H]+=420.1, tR=2.013 min.

Workup

  1. customthe reaction by LCMS and TLC
  2. extractionNaHCO3 aqueous until the pH to 8˜9 and extracted with DCM for three times
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-c5e9dbac1c104868a2e9a12096e412ed
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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