Hydrochloric Acid → HCID 86695407, compound

HRID 1487454Notes

Reaction equation

HRID 1487454 reaction equation
C([N:4]([CH:7]([CH3:9])C)[CH2:5]C)(C)C.CS(O[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C@H:28]3[O:32]C(C)(C)[N:30]([C:35](=[O:39])[CH:36]([Cl:38])[Cl:37])[C@@H:29]3[CH2:40][F:41])=[CH:24][CH:23]=2)=[CH:18][N:17]=1)(=O)=O.N1CCC1.Cl>CN(C)C=O>[N:4]1([CH2:15][C:16]2[N:17]=[CH:18][C:19]([C:22]3[CH:23]=[CH:24][C:25]([C@@H:28]([OH:32])[C@H:29]([NH:30][C:35](=[O:39])[CH:36]([Cl:38])[Cl:37])[CH2:40][F:41])=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)[CH2:5][CH2:9][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 86695408HCID 86695408, compound

Product 1

HCID 86695407HCID 86695407, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Diisopropylethylamine (296 μL, 1.68 mmol) is added to the product of Example 20, Step 2 (50 mg, 0.11 mmol) and azetidine.HCl salt (146 mg, 1.12 mmol) in dimethylformamide (1 mL) and the mixture heated to 60° C. for 4 hours. The solvent is removed under reduced pressure and the residue dissolved in CH2Cl2 (2 mL). The mixture is cooled to 0° C. and trifluoroacetic acid (2 mL) added. After 1 hour, the solvent is removed under reduced pressure and the crude product purified using reverse phase HPLC to give the title compound (10 mg): m/z (CI) M−H 425.1.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved in CH2Cl2 (2 mL)
  3. additiontrifluoroacetic acid (2 mL) added
  4. customthe solvent is removed under reduced pressure
  5. customthe crude product purified

Sources & evidence

ORD record
ord-176a1cb2e5604c6da57bfe183931d58e
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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