Water → HCID 67312440, compound

HRID 1256121Notes

Reaction equation

HRID 1256121 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]([OH:11])=O)[CH:7]=1.[CH2:26]([NH:30][CH3:31])[CH2:27][CH2:28][CH3:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.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]([N:30]([CH2:26][CH2:27][CH2:28][CH3:29])[CH3:31])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8068N-MethylbutylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 67312440HCID 67312440, compoundYield 27%

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 (360 mg, 1 mmol) and n-butylmethylamine (0.6 mL, 6 mmol) in 10 mL of DMF was added PyBOP (780 mg, 1.5 mmol) and TEA (0.5 mL, 3.56 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 first purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a yellow solid (115 mg, yield 27%). MS calcd for (C20H26BN3O5S): 431.2. MS found (ESI negative): (M−H)−=430.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.80 (s, 1H), 9.17 (bs, 1H), 7.45 (m, 2H), 7.22 (d, J=8 Hz, 1H), 7.11 (d, J=8, 2 Hz, 1H), 6.37 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 5.94 (bs, 2H), 4.87 (s, 2H), 3.77 (s, 2H), 3.15 (m, 2H), 2.85 (s, 3H), 1.39 (m, 2H), 1.30 (m, 2H), 0.87 (t, J=7.2 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 first purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-069ca2c57e11493da35b1b4e4320a066
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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