Ammonium Chloride → HCID 10393085, compound

HRID 1827319Notes

Reaction equation

HRID 1827319 reaction equation
[CH2:1]([N:8]([CH:13]1[CH2:22][C:21]2[C:16](=[C:17]([C:25]([C:27]3[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=3)=[O:26])[CH:18]=[C:19]([C:23]#[N:24])[CH:20]=2)[O:15][CH2:14]1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([Mg]Br)=[CH:36][CH:35]=1.[NH4+].[Cl-]>O1CCCC1>[CH2:1]([N:8]([CH:13]1[CH2:22][C:21]2[C:16](=[C:17]([C:25]([C:37]3[CH:38]=[CH:39][C:34]([Cl:33])=[CH:35][CH:36]=3)([OH:26])[C:27]3[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=3)[CH:18]=[C:19]([C:23]#[N:24])[CH:20]=2)[O:15][CH2:14]1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10343750HCID 10343750, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 10393085HCID 10393085, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To suspension of Example 7 (25 mg, 0.5 mmol) in tetrahydrofuran (0.5 mL) at 0° C. was added a solution of p-chlorophenyl magnesium bromide (1M in ether, 0.1 mL, 0.1 mmol). After stirring for 2 h at RT, the mixture was treated with NH4Cl solution and extracted with dichloromethane. The combined organic extracts were dried, concentrated and the residue was purified by reverse phase preparative HPLC. The appropriate fraction were mixed, concentrated and converted to HCl salt to afford the title compound (25 mg, 87%). LC/MS: (M+H)+=561, 563 (3:1 ratio).

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated
  4. customthe residue was purified by reverse phase preparative HPLC
  5. additionThe appropriate fraction were mixed
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8df7313038764e9cbaee43e3cbe91cdc
Source dataset
uspto-grants-2006_05
Patent number
US07053223B2

Reaction notes

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