Ammonia → HCID 70564591, compound

HRID 1477935Notes

Reaction equation

HRID 1477935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([O:11]C)=O)=[CH:4][CH:3]=1.[NH3:30]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH2:28][CH3:29])(=[O:26])=[O:27])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([NH2:30])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 70562192HCID 70562192, compound

Product 1

HCID 70564591HCID 70564591, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step A above (0.43 g, 1.0 mmol) was dissolved in a 7 N solution of ammonia in methanol (25 mL). After stirring at RT for 10 h, the resulting mixture was concentrated under reduced pressure. The residue was dissolved in dioxane/water, acidified with TFA, and purified directly on RP-HPLC to give the title compound. LC/MS m/z=420.1 [M+H]+. The two enantiomers were separated by SFC chiral separation.

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dioxane/water
  3. custompurified directly on RP-HPLC

Sources & evidence

ORD record
ord-247b4dc5fef94a568cf8e61d4a78bb18
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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