Pyridine → HCID 53234455, compound

HRID 1256109Notes

Reaction equation

HRID 1256109 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.N1C=CC=CC=1.Cl[S:19]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])=[CH:24][C:23]=1[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=[O:21])=[O:20]>C(Cl)Cl>[OH:10][B:7]1[C:6]2[CH:11]=[C:2]([NH:1][S:19]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:34])[C:30]([F:31])([F:32])[F:33])=[CH:24][C:23]=3[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=[O:20])=[O:21])[CH:3]=[CH:4][C:5]=2[CH2:9][O:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655216HCID 86655216, compound

Product 1

HCID 53234455HCID 53234455, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (0.7 g, 4.7 mmol), pyridine (1 mL, 12.4 mmol) in DCM (10 mL) was added ethyl 2-(2-(chlorosulfonyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (1.5 g, 4 mmol). The reaction was stirred at r.t. for 2 hr and monitored by LC/MS. Purification: The solvent was removed and worked up with EtOAc and 1N HCl, brine, dried over Na2SO4. A portion of the crude material was purified by the preparative HPLC give the title product ethyl 2-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate 18 mg as white powder 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.54 (s, 1H), 10.36 (s, 1H), 9.21 (bs, 1H), 7.85 (d, J=8 Hz, 1H), 7.71 (m, 2H), 7.44 (d, J=2 Hz, 1H), 7.25 (d, J=8.4 Hz, 1H), 7.12 (dd, J=8, 2 Hz, 1H), 4.87 (s, 2H), 4.06 (m, 4H), 1.17 (t, J=7.2 Hz, 3H); MS (ESI) m/z=485.1 (M−H, negative).

Workup

  1. customPurification
  2. customThe solvent was removed
  3. dry with materialdried over Na2SO4
  4. customA portion of the crude material was purified by the preparative HPLC

Sources & evidence

ORD record
ord-69ccabbe50804cd283f018ea97d04acc
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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