Butylamine → HCID 67312166, compound

HRID 1256119Notes

Reaction equation

HRID 1256119 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.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O.CO>[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:30][CH2:26][CH2:27][CH2:28][CH3:29])=[O:10])[CH:7]=1

Participants

7

Reactant 3

HCID 8007ButylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 67312166HCID 67312166, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×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-butylamine (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 ISCO CombiFlash Rf silica chromatography eluted with 88:10:2 chloroform:MeOH:H2O to give the desired product as a yellow solid (228 mg, yield 54%). MS calcd for (C19H24BN3O5S): 417.2. MS found (ESI negative): (M−H)−=416.2. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.88 (s, 1H), 9.17 (s, 1H), 7.96 (t, J=5.2 Hz, 1H), 7.42 (m, 2H), 7.22 (d, J=8 Hz, 1H), 7.11 (dd, J=8, 2 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 6.35 (dd, J=2.4, 8.8 Hz, 1H), 5.93 (bs, 2H), 4.87 (s, 2H), 3.77 (s, 2H), 3.08 (m, 2H), 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 ISCO CombiFlash Rf silica chromatography
  6. washeluted with 88:10:2 chloroform

Sources & evidence

ORD record
ord-1eb5eefdd78f4877a7505d5e33d15b7b
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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