Triethylamine → HCID 86281797, compound

HRID 2275422Notes

Reaction equation

HRID 2275422 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5](Cl)=[O:6].[C:12]([NH:16][NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[CH2:27][O:26][B:25]([OH:28])[C:24]=2[C:29]=1[F:30])=[O:19])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(OCC)C>[C:12]([N:16]([C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[CH:8]=1)[NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[CH2:27][O:26][B:25]([OH:28])[C:24]=2[C:29]=1[F:30])=[O:19])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810883,5-Dimethylbenzoyl ChlorideHCID 90408067HCID 90408067, compound

Product 1

HCID 86281797HCID 86281797, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,5-dimethylbenzoyl chloride (0.076 g, 0.451 mmol) in a round bottom flask was dissolved in diethyl ether (2.0 ml). To this, N′-(tert-butyl)-7-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbohydrazide (0.100 g, 0.376 mmol) was added following by TEA (0.105 ml, 0.752 mmol). After triethyl amine addition a precipitant came out of solution. After 90 min of stirring, another equivalent of TEA was added and reaction was allowed to stir for 60 min at room temperature. The solvent was evaporated and the residue was purified by using preparative HPLC to give Cpd. No. 58. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 6.97 (d, J=7.7 Hz, 1H), 6.89-6.83 (m, 3H), 6.72-6.64 (m, 1H), 4.76 (s, 2H), 2.04 (d, J=4.5 Hz, 6H), 1.29 (s, 9H).

Workup

  1. additionanother equivalent of TEA was added
  2. customreaction
  3. stirringto stir for 60 min at room temperature
  4. customThe solvent was evaporated
  5. customthe residue was purified
  6. customto give Cpd

Sources & evidence

ORD record
ord-bc8240c696664f4f9421c52370e9d68a
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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