Triethylamine → HCID 86594555, compound

HRID 1744088Notes

Reaction equation

HRID 1744088 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:24]([NH:25][C@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:23][O:22][N:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:35][CH2:36][C:37]#[N:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:36]([CH2:37][NH:38][C:31](=[O:33])[C@H:26]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH:25][C:24]1[C:20]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3)=[CH:19][CH:18]=2)=[N:21][O:22][CH:23]=1)#[N:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 69151518HCID 69151518, compound

Product 1

HCID 86594555HCID 86594555, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of N-(3-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}isoxazol-4-yl)leucine (46 mg, 0.10 mmol), aminoacetonitrile hydrochloride (21 mg, 0.23 mmol) and HATU. (140 mg, 0.36 mmol) in DMF (3 mL) was added triethylamine (0.06 mL, 0.43 mmol). The solution was stirred 1 h, then partitioned between ether and pH 3.5 phosphate buffer. The organic phase was washed with brine and concentrated. Purification by flash chromatography (40% to 60% ethyl acetate/hexanes) gave 15.5 mg of N1-(cyanomethyl)-N2-[3-(4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl)isoxazol-4-yl]leucinamide.

Workup

  1. customTo a 0° C.
  2. custompartitioned between ether and pH 3.5 phosphate buffer
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. customPurification by flash chromatography (40% to 60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-70878358caae40ba85671c9e3a993b5a
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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