Trifluoroacetic acid → HCID 10368941, compound

HRID 2233155Notes

Reaction equation

HRID 2233155 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([S:20]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31]C)[CH2:25][CH2:24]2)(=[O:22])=[O:21])[C:14]=1[OH:33])=[O:11].FC(F)(F)C(O)=O.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([S:20]([N:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][OH:31])[CH2:27][CH2:28]2)(=[O:22])=[O:21])[C:14]=1[OH:33])=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 25134Boron tribromideHCID 67077117HCID 67077117, compound

Product 1

HCID 10368941HCID 10368941, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under Ar, to the suspension of 2c trifluoroacetic acid salt (100 mg, 0.16 mmol) in 3 mL of dichloromethane was added boron tribromide (0.63 mL, 0.63 mmol). The mixture was stirred at room temperature overnight. After quenching with methanol, solid produced. The mixture was filtered, solid was collected. Purification upon Gilson HPLC, eluting with acetonitrile/water/0.1% TFA (10/90, v/v to 90/10, v/v, over 10 min) yielding 66 mg (76%) of the title compound 2d. LC-MS (m/z) 507.2 (M+H).

Workup

  1. customAfter quenching with methanol, solid
  2. customproduced
  3. filtrationThe mixture was filtered
  4. customsolid was collected
  5. customPurification upon Gilson HPLC
  6. washeluting with acetonitrile/water/0.1% TFA (10/90, v/v to 90/10

Sources & evidence

ORD record
ord-13e2c9eee2d94beb90060effb67c9335
Source dataset
uspto-grants-2010_05
Patent number
US07709485B2

Reaction notes

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