Boron Trichloride → HCID 53241566, compound

HRID 1914907Notes

Reaction equation

HRID 1914907 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:12][CH:11]1[S:13]([NH:16][C:17]1[C:25]2[O:24][CH:23]=[N:22][C:21]=2[C:20]([F:26])=[C:19]([F:27])[C:18]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=1[F:36])(=[O:15])=[O:14])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]([CH:11]2[CH2:12][CH:10]2[CH2:9][OH:8])(=[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 53241565HCID 53241565, compound

Product 1

HCID 53241566HCID 53241566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 1L was prepared from 2-(benzyloxymethyl)-N-(4,5-difluoro-6-(2-fluoro-4-iodophenylamino)benzo[d]oxazol-7-yl)cyclopropane-1-sulfonamide (150 mg, 0.238 mmol) in DCM (10 mL) was reacted with 1.0M solution of BCl3 in DCM (0.9 mL, 0.952 mmol) to afford the crude product. The reaction mixture was quenched with methanol (0.5 mL) and partitioned between water and ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous Na2SO4 and concentrated. Purification by column chromatography on silica gel (60-100% ethyl acetate in hexane) afforded 65 mg of the product (54% yield). H1NMR (CDCl3, 300 MHz): δ 7.7-7.6 (bs, 1H), 7.4-7.3 (m, 1H), 7.3-7.2 (m, 1H), 6.6 (s, 1H), 6.2 (s, 1H), 6.2-6.0 (m, 1H), 3.1-3.0 (t, 1H), 4.2-4.0 (m, 2H), 2.6-2.5 (m, 1H), 1.5-1.4 (m, 1H), 1.0-0.9 (m, 2H). LCMS: 100%, m/z=539.6 (M+H). HPLC: 83.1%

Workup

  1. customto afford the crude product

Sources & evidence

ORD record
ord-62b2977d6c564e499bbe2172fa1c8122
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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