Hydrochloric Acid → HCID 118250211, compound

HRID 522523Notes

Reaction equation

HRID 522523 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:17]=[C:16]([C:18]([Cl:21])([Cl:20])[Cl:19])[N:15]=[C:14]([N:22]4[CH2:27][CH:26]5[CH2:28][CH2:29][CH:23]4[CH2:24][N:25]5C(OC(C)(C)C)=O)[N:13]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[ClH:19].[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:17]=[C:16]([C:18]([Cl:20])([Cl:19])[Cl:21])[N:15]=[C:14]([N:22]4[CH2:27][CH:26]5[CH2:28][CH2:29][CH:23]4[CH2:24][NH:25]5)[N:13]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117603132HCID 117603132, compound

Product 1

HCID 118250211HCID 118250211, compoundYield 181.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Deprotected a solution of the product of Step 1 (1.1 g, 1.98 mmol) in anhydrous CHCl3 (18 mL) with 4N HCl in dioxane (18 mL, 71.6 mmol) under N2. Stirred at room temperature for >18 h, then concentrated. Added diethyl ether (60 mL) and CH2Cl2 (5 mL) and stirred for 1 h. Filtered resulting solid, washed with ether and CH2Cl2, and dried to give the title compound (0.88 g) as a yellow solid. MS, calc'd=452.10. Obsv'd m/z: 453.10 (M+1).

Workup

  1. concentrationconcentrated
  2. stirringAdded diethyl ether (60 mL) and CH2Cl2 (5 mL) and stirred for 1 h
  3. filtrationFiltered
  4. customresulting solid
  5. washwashed with ether and CH2Cl2
  6. customdried

Sources & evidence

ORD record
ord-9b35cb67b8e4431fa125e49800429f5d
Source dataset
uspto-grants-2016_05
Patent number
US09334246B2

Reaction notes

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