Isobutyric Acid → HCID 66673600, compound

HRID 423695Notes

Reaction equation

HRID 423695 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH3:33][CH:34]([CH3:38])[C:35](O)=[O:36].C(N(C(C)C)CC)(C)C.[CH3:48][S:49]([C:52]1[CH:57]=[CH:56][C:55]([C:58]2[N:63]=[CH:62][C:61]([O:64][CH2:65][CH:66]3[CH2:71][CH2:70][N:69]([C:72]([NH:74][NH2:75])=[O:73])[CH2:68][CH2:67]3)=[CH:60][CH:59]=2)=[CH:54][CH:53]=1)(=[O:51])=[O:50]>CN(C=O)C.O>[CH3:33][CH:34]([CH3:38])[C:35]([NH:75][NH:74][C:72]([N:69]1[CH2:68][CH2:67][CH:66]([CH2:65][O:64][C:61]2[CH:62]=[N:63][C:58]([C:55]3[CH:56]=[CH:57][C:52]([S:49]([CH3:48])(=[O:50])=[O:51])=[CH:53][CH:54]=3)=[CH:59][CH:60]=2)[CH2:71][CH2:70]1)=[O:73])=[O:36]

Participants

8

Reactant 5

HCID 6590Isobutyric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66673247HCID 66673247, compound

Product 1

HCID 66673600HCID 66673600, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

TBTU (279 mg, 0.87 mmol) and HOBT (24 mg, 0.17 mmol) were added to a mixture of 2-methylpropanoic acid (81 μL, 0.87 mmol), diisopropylethylamine (0.758 mL, 4.35 mmol) in DMF (5 mL) at ambient temperature. The mixture was stirred at ambient temperature for 15 min. The mixture was charged with 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide (352 mg, 0.87 mmol), and was stirred at ambient temperature overnight. The mixture was charged with water and set at ambient temperature overnight. The resulting tan precipitate was filtered, washed with water, and dried in a vacuum oven to give 350 mg (85%) of N′-(2-methylpropanoyl)-4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 9.31 (d, 1H, J=1.9 Hz), 8.44 (d, 1H, J=2.9 Hz), 8.36 (d, 1H, J=1.9 Hz), 8.29 (d, 2H, J=8.6 Hz), 8.06 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.08-3.96 (m, 4H), 3.25 (s, 3H), 2.80-2.70 (m, 2H), 2.41 (septet, 1H, J=6.8 Hz), 2.08-1.92 (m, 1H), 1.82-1.73 (m, 2H), 1.30-1.10 (m, 2H), 1.02 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 475 (M+H).

Workup

  1. stirringwas stirred at ambient temperature overnight
  2. waitset at ambient temperature overnight
  3. filtrationThe resulting tan precipitate was filtered
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ef83a6e1efad4b72b240371166a346d3
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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