Water → HCID 67311405, compound

HRID 1256116Notes

Reaction equation

HRID 1256116 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.Cl.CN.C1C[N:32]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:31]C1.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([NH:32][CH3:31])=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2724699PyBOPHCID 6364545Methylamine hydrochlorideHCID 53234452HCID 53234452, compound

Product 1

HCID 67311405HCID 67311405, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (860 mg, 2.37 mmol) and methylamine hydrochloride salt (0.34 g, 4.75 mmol) in 10 mL of DMF was added PyBOP (1300 mg, 2.49 mmol) and TEA (1.13 mL, 8.3 mmol). The reaction mixture was stirred for 16 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as an offwhite powder (165 mg, yield 19%). MS calcd for (C16H18BN3O5S): 375.1. MS found (ESI negative): (M−H)−=374.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.87 (s, 1H), 9.17 (bs, 1H), 7.93 (d, J=4.8 Hz, 1H), 7.41 (m, 2H), 7.22 (d, J=8 Hz, 1H), 7.11 (dd, J=8, 2 Hz, 1H), 6.45 (d, J=2.4 Hz, 1H)), 6.35 (d, J=8.8, 2 Hz, 1H), 4.87 (s, 2H), 3.77 (s, 2H), 2.63 (d, J=4.4 Hz, 3H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-8f56815dd22e460ba8e148d9c5582a6d
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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