Ethylamine → HCID 67312270, compound

HRID 1256117Notes

Reaction equation

HRID 1256117 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]([NH2:28])[CH3:27].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[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:28][CH2:26][CH3:27])=[O:11])[CH:7]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 67312270HCID 67312270, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (500 mg, 1.4 mmol) and ethyl amine (2.1 mg, 4.2 mmol) in DMF (5 ml), added PyBOP (730 mg, 1.4 mmol) then triethyl amine (0.4 ml, 3 mmol). Stirring was kept for 3 hours. Diluted with EtOAc, washed with 1N HCl, water and brine. Dried over anhydrous sodium sulfate. Concentrated, the residue was dissolved in DMSO and purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column). The title compound was obtained as white powder. MS calcd for (C17H20BN3O5S): 389.12. MS found (ESI negative): (M−H)−=388.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.86 (s, 1H), 9.15 (br, 1H), 7.98 (m, 1H), 7.41 (s, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.21 (d, J=8 Hz, 1H), 7.09 (dd, J=8.4 Hz, 1H), 6.44 (d, J=2 Hz, 1H), 6.33 (dd, J=8.8 Hz, 1H), 4.85 (s, 2H), 3.75 (s, 2H), 3.09 (m, 1H), 1.02 (t, J=7.2 Hz, 3H).

Workup

  1. washwashed with 1N HCl, water and brine
  2. dry with materialDried over anhydrous sodium sulfate
  3. concentrationConcentrated
  4. dissolutionthe residue was dissolved in DMSO
  5. custompurified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-0dcacb05888846b88c1acc05b9e66c2c
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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