Hydrochloric Acid → HCID 86711861, compound

HRID 623775Notes

Reaction equation

HRID 623775 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]1[C:24]([N:26]([CH2:28][C:29]([C:32](=O)[NH2:33])([CH3:31])[CH3:30])[CH3:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.Cl.C(Cl)Cl>N1C=CC=CC=1>[CH2:1]([N:8]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]1[C:24]([N:26]([CH2:28][C:29]([C:32]#[N:33])([CH3:30])[CH3:31])[CH3:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6344DichloromethaneHCID 9845Trifluoroacetic anhydrideHCID 86711860HCID 86711860, compound

Product 1

HCID 86711861HCID 86711861, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of SC-174 (235 mg, 0.478 mmol) in pyridine (4.83 mL) was added at 0° C. TFAA (0.153 mL, 1.099 mmol) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 30 min. Aqueous 1 M HCl (20 mL) and DCM (10 mL) were added and the aqueous layer was set to pH 2 with aqueous 5 M HCl (10 mL). The layers were separated and extracted twice with DCM (10 mL). The combined organic layers were concentrated in vacuo. Purification was performed with flash chromatography (silica, gradient heptane/EtOAc, 1:0→0:1). The appropriate fractions were combined and solvents removed in vacuo to give SC-187 (187 mg, 82%) as a yellow foam.

Workup

  1. customThe layers were separated
  2. extractionextracted twice with DCM (10 mL)
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. customPurification
  5. customsolvents removed in vacuo

Sources & evidence

ORD record
ord-7e890be061bb45ab84a8b77defc4d77e
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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