Triethylamine → HCID 67311321, compound

HRID 1256127Notes

Reaction equation

HRID 1256127 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.Cl.[NH:27]1[CH2:30][CH2:29][CH2:28]1.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]([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)(=[O:25])=[O:24])=[C:6]([CH2:8][C:9]([N:27]2[CH2:30][CH2:29][CH2:28]2)=[O:11])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 12308726Azetidine hydrochlorideHCID 53234452HCID 53234452, compound

Product 1

HCID 67311321HCID 67311321, 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 azetidine hydrochloride (470 mg, 5 mmol) in DMF (5 ml), added PyBOP (730 mg, 1.4 mmol) then triethyl amine (1.1 ml, 8 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 compound was obtained as white powder. MS calcd for (C18H20BN3O5S): 401.12. MS found (ESI negative): (M−H)−=400.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.69 (s, 1H), 7.36 (d, J=1.6 Hz, 1H), 7.34 (d, J=8.8 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 7.04 (dd, J=8.4 Hz, 1H), 6.34 (d, J=2.4 Hz, 1H), 6.30 (dd, J=8.8 Hz, 1H), 4.81 (s, 2H), 4.01 (t, J=7.2 Hz, 1H), 3.81 (t, J=7.6 Hz, 1H), 3.57 (s, 2H), 2.11 (m, 2H).

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)
  6. customThe compound was obtained as white powder

Sources & evidence

ORD record
ord-6427bfbb0ff24ad8beb924cbafbfcb5b
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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