Diisopropylethylamine → HCID 67268025, compound

HRID 602518Notes

Reaction equation

HRID 602518 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH3:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[N:61]1([CH2:67][C:68](O)=[O:69])[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:68](=[O:69])[CH2:67][N:61]2[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]2)=[C:21]([CH3:26])[CH:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 201097Piperidin-1-yl-acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67266881HCID 67266881, compound

Product 1

HCID 67268025HCID 67268025, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-amino-3-methylphenyl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (15.2 mg, 40 mol) in DMF (100 μL) was added a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 27.4 mg, 72 mol) in DMF (100 μL), followed by i-Pr2NEt (25 μL, 144 mol) and piperidin-1-yl-acetic acid (8.6 mg, 60 mol). The resulting mixture was shaken at room temperature for 3 hours after which it was diluted with ethyl acetate (10 mL), washed with saturated aqueous ammonium chloride (2×10 mL), dried over sodium sulfate, and evaporated. The residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield [3-methyl-4-(2-piperidin-1-yl-acetylamino)-phenyl]-(4-trifluoromethylbenzyl)-carbamic acid tert-butyl ester as a white solid (10.7 mg, 53%). This was dissolved in dichloromethane (200 μL) and trifluoroacetic acid (200 μL), and the solution was kept at room temperature for 30 minutes, after which volatiles were evaporated and the residue was dried in vacuo at 0.1 mmHg and +40° C. for 1 hour. The resulting trifluoroacetic acid addition salt of the title compound was obtained as a yellow semisolid in quantitative yield.

Workup

  1. washwashed with saturated aqueous ammonium chloride (2×10 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-e8a4c14ebd344fbfad9a8ceebf8d5dce
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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