Boron Trichloride → HCID 118062201, compound

HRID 920766Notes

Reaction equation

HRID 920766 reaction equation
C([O:8][CH:9]1[CH2:12][C:11]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]3[N:23]=[C:24]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Cl:36])[CH:30]=4)[C:25]([C:26]([NH2:28])=[O:27])=[C:19]3[CH2:18]2)=[O:16])([CH3:13])[CH2:10]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:36][C:31]1[CH:30]=[C:29]([C:24]2[C:25]([C:26]([NH2:28])=[O:27])=[C:19]3[CH2:18][N:17]([C:15]([NH:14][C:11]4([CH3:13])[CH2:10][CH:9]([OH:8])[CH2:12]4)=[O:16])[CH2:22][CH2:21][N:20]3[N:23]=2)[CH:34]=[CH:33][C:32]=1[F:35]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 123350859HCID 123350859, compound

Product 1

HCID 118062201HCID 118062201, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 260A (70 mg, 0.137 mmol) in DCM (10 mL), cooled to −78° C., was added BCl3 (0.547 ml, 0.547 mmol, 1.0 M in DCM) and the resulting mixture was allowed to warm to RT and stir for 16 h. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl and extracted with DCM (3×25 mL). The combined organic layers were dried over Na2SO4 and evaporated. The crude compound was purified by preparative HPLC to afford Compound 260 as an off-white solid (9.0 mg, 16% yield). HPLC Ret. Times 6.51 min. and 6.54 min. (HPLC Methods A and B). MS(ES): m/z=422 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.86 (dd, J=7.31, 2.16 Hz, 1H), 7.69 (dt, J=6.24, 2.49 Hz, 1H), 7.43-7.48 (t, 1H), 7.11-7.41 (m, 2H), 6.96 (s, 1H), 6.68 (s, 1H), 4.90 (dd, J=10.42, 6.15 Hz, 1H), 4.70 (s, 2H), 4.08-4.18 (m, 2H), 3.97 (m, 1H), 3.82 (s, 2H), 2.45-2.56 (m, 1H), 2.26-2.38 (m, 1H), 1.95-1.98 (m, 1H), 1.70-1.75 (m, 1H), 1.74 (s, 1.5H), 1.24-1.40 (s, 1.5H).

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous solution of NH4Cl
  2. extractionextracted with DCM (3×25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customThe crude compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-cf7b03f517924518afa3522add6e7dae
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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