Hydrochloric Acid → HCID 71536097, compound

HRID 2175143Notes

Reaction equation

HRID 2175143 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]5[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=5)[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>CO>[CH3:40][N:38]1[CH:39]=[C:35]([C:32]2[CH:33]=[CH:34][C:29]3[N:30]([C:26]([S:25][C:21]4[CH:22]=[C:23]5[C:18](=[CH:19][CH:20]=4)[N:17]=[CH:16][C:15]([N:12]4[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]4)=[CH:24]5)=[N:27][N:28]=3)[CH:31]=2)[CH:36]=[N:37]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86696262HCID 86696262, compound

Product 1

HCID 71536097HCID 71536097, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (49.1) (48.5 mg, 0.085 mmol) in MeOH (2 mL) was added HCl solution in MeOH (1M) (5 mL, 5.00 mmol). The reaction mixture was stirred at rt for 1 h, quenched with saturated NaHCO3 solution and extracted with extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, concentrated, purified via biotage by flash chromatography on silica gel using a gradient of 0-10% MeOH/CH2Cl2 to give the title compound (38 mg, 0.083 mmol, 98% yield). [Method 1E]

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionextracted
  3. extractionwith extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified via biotage by flash chromatography on silica gel using a gradient of 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-36e9bbb7ef1e4eb3bff3c58979d3c5bc
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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