Triethylamine → HCID 53234536, compound

HRID 1256132Notes

Reaction equation

HRID 1256132 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.NN.C1CN([P+](O[N:45]2[N:53]=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[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:24])=[O:25])=[C:6]([CH2:8][C:9]([NH:45][NH2:53])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 53234536HCID 53234536, compoundYield 20.1%

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 (23.6 mg, 0.066 mmol) and hydrazine (6.3 uL, 0.13 mmol) in 1 mL of DMF were added PyBOP (69 mg, 0.13 mmol) and triethylamine (31 uL, 0.22 mmol). The reaction mixture was stirred at room temperature for 1 hour. The crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as a white solid (5.0 mg, yield 16%). MS calcd for (C15H17BN4O5S): 376.1. MS found (ESI negative): (M−H)−=375.1. 1H NMR (DMSO-d6) δ (ppm): 10.4 (bs, 1H), 9.74 (s, 1H), 9.11 (bs, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.36 (s, 1H), 7.17 (d, J=8.0 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 6.34 (m, 2H), 5.89 (bs, 2H), 4.81 (s, 2H), 3.76 (s, 2H).

Workup

  1. customThe crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-0dd5f98093bc4631bf05b8500baad82a
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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