Diisopropylethylamine → HCID 118483098, compound

HRID 1773345Notes

Reaction equation

HRID 1773345 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([Cl:13])[N:7]=[C:6]1Cl.[C:16]([O:20][C:21](=[O:29])[NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([Cl:13])[N:7]=[C:6]1[N:26]1[CH2:25][CH2:24][CH:23]([NH:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:29])[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 118483096HCID 118483096, compound

Product 1

HCID 118483098HCID 118483098, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2,4,5-trichloro-6-oxo-6H-pyrimidin-1-yl)-acetic acid methyl ester (6.0 g, 22.4 mmol) and piperidin-4-yl-carbamic acid tert-butyl ester (4.9 g, 24.4 mmol) in DMF (50 mL) was added DIPEA (5.7 g, 44.3 mmol) dropwise at RT, and the mixture was stirred overnight. The reaction mixture was diluted with water (500 mL), and the solids were collected by filtration. The solids were then dissolved in DCM (100 mL), washed with water (100 mL, 3×), washed with brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified by silica chromatography (1:2 to 1:1, DCM:PE) to give 6.3 g of the title product (64%). 1H NMR (400 MHz, CDCl3): δ 1.22-1.34 (m, 2H), 1.45 (s, 9H), 1.97-2.03 (m, 2H), 2.96-3.09 (m, 2H), 3.68-3.69 (m, 1H), 3.75 (s, 3H), 4.42-4.44 (m, 3H), 4.84 (s, 2H). [M+H] Calc'd for C17H24Cl2N4O5, 435. Found, 435.

Workup

  1. filtrationthe solids were collected by filtration
  2. dissolutionThe solids were then dissolved in DCM (100 mL)
  3. washwashed with water (100 mL, 3×)
  4. washwashed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography (1:2 to 1:1, DCM:PE)

Sources & evidence

ORD record
ord-3ab36978a923415c9e0a9bb016dd14db
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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