Boron Trichloride → HCID 53241567, compound

HRID 1914908Notes

Reaction equation

HRID 1914908 reaction equation
C([O:8][CH2:9][C:10]1([S:13]([NH:16][C:17]2[C:25]3[O:24][CH:23]=[N:22][C:21]=3[C:20]([F:26])=[C:19]([F:27])[C:18]=2[NH:28][C:29]2[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[F:36])(=[O:15])=[O:14])[CH2:12][CH2:11]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[F:26][C:20]1[C:21]2[N:22]=[CH:23][O:24][C:25]=2[C:17]([NH:16][S:13]([C:10]2([CH2:9][OH:8])[CH2:12][CH2:11]2)(=[O:15])=[O:14])=[C:18]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[F:36])[C:19]=1[F:27]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 53241672HCID 53241672, compound

Product 1

HCID 53241567HCID 53241567, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(Benzyloxymethyl)-N-(4,5-difluoro-6-(2-fluoro-4-iodophenylamino)-benzo[d]oxazol-7-yl)cyclopropane-1-sulfonamide (100 mg, 0.158 mmol) in DCM (10 mL) was reacted with 1.0M solution of BCl3 in DCM (0.476 mL, 0.476 mmol) to afford the crude product. The reaction mixture was quenched with ice and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous Na2SO4 and concentrated. Purification by preparative TLC (70% ethyl acetate in hexane) afforded 35 mg of the product (42% yield). H1NMR (CDCl3, 300 MHz): δ 8.1 (s, 1H), 7.4 (d, 1H), 7.3-7.2 (m, 1H), 7.1 (s, 1H), 6.8 (s, 1H), 6.5-6.4 (m, 1H), 4.1 (s, 2H), 2.7 (s, 1H), 1.4 (t, 2H), 1.0 (t, 2H). LCMS: 97.25%, m/z=537.8 (M−11). HPLC: 95.5%

Workup

  1. customto afford the crude product
  2. customThe reaction mixture was quenched with ice
  3. extractionextracted
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customPurification by preparative TLC (70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7bc2ca290d9d4d519dbe1ab535f7e9be
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

Loading…