Diisopropylethylamine → HCID 57619803, compound

HRID 1642496Notes

Reaction equation

HRID 1642496 reaction equation
[CH3:1][C:2]1([N:15]2[CH2:20][CH2:19][CH:18]([NH:21][C@H:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]3[CH2:28][C:29](O)=[O:30])[CH2:17][CH2:16]2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[O:30]=[C:29]1[CH2:28][C@@H:23]2[C@H:22]([CH2:27][CH2:26][CH2:25][CH2:24]2)[N:21]1[CH:18]1[CH2:17][CH2:16][N:15]([C:2]2([CH3:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:6][CH2:7]2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57619830HCID 57619830, compound

Product 1

HCID 57619803HCID 57619803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(1R,2S)-2-[[1-[4-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-piperidyl]-4-piperidyl]amino]cyclohexyl]acetic acid, diisopropylethylamine (0.5 mL, 3.36 mmol) and HATU (0.7 g, 1.84 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction quenched with water and concentrated in vacuo. The residue was diluted in ethylacetate (100 mL) and washed with 1N NaOH (10 mL). The organic phase was separated and aqueous phase was extracted with ethylacetate (2×30 mL). The combined organic phases were dried and concentrated in vacuo to provide the title compound. MS (M+1): 420.38.

Workup

  1. customThe reaction quenched with water
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted in ethylacetate (100 mL)
  4. washwashed with 1N NaOH (10 mL)
  5. customThe organic phase was separated
  6. extractionaqueous phase was extracted with ethylacetate (2×30 mL)
  7. customThe combined organic phases were dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fb93d8366364bd581bc992bcf0148bf
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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