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Triethylamine → 2-[4-(4-Methoxy-3-methyl-benzoyl)-piperidin-1-yl]-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide

HRID 713530
Notes
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Reaction equation

HRID 713530 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[CH3:21].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:51][CH2:52][C:53]1[NH:54][C:55](=[O:63])[C:56]2[CH2:62][O:61][CH2:60][CH2:59][C:57]=2[N:58]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:51][CH2:52][C:53]3[NH:54][C:55](=[O:63])[C:56]4[CH2:62][O:61][CH2:60][CH2:59][C:57]=4[N:58]=3)=[O:18])[CH2:13][CH2:14]2)=[O:8])=[CH:5][C:4]=1[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71227025[4-(4-Methoxy-3-methyl-benzoyl)-piperidin-1-yl]-acetic acidHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 1

HCID 136237339
2-[4-(4-Methoxy-3-methyl-benzoyl)-piperidin-1-yl]-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide
Yield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(4-methoxy-3-methyl-benzoyl)-piperidin-1-yl]-acetic acid (0.10 g, 0.34 mmol), EDCl (0.08 g, 0.41 mmol), HOBT (0.06 g, 0.41 mmol) and triethylamine (0.17 g, 1.7 mmol) in 10 mL of DMF was stirred at ambient temperature for 20 min., then 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (0.06 g, 0.34 mmol) was added. The reaction mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted with 50 mL of water, extracted with DCM (100 mL) and the combined organic layers were washed with saturated aqueous NaHCO3 solution. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to provide crude product. Purification by flash chromatography gave the title compound (42.8 mg, 0.09 mmol) as a yellow solid. MS (ESI) m/z 454.8 (M+H+); HPLC (Insertsil ODS3 100×3 mm C-18 column: mobile phase: 5-95% acetonitrile/water with 0.1% TFA, at 1 mL/min over 7.75 min.), t=1.21 min. 1H NMR (400 MHz, dichloromethane-d2) δ ppm 1.77-1.97 (m, 4H), 2.28 (br. s., 3H), 2.42-2.55 (m, 2H), 2.64-2.77 (m, 2H), 2.90-3.11 (m, 3H), 3.17-3.24 (m, 2H), 3.25-3.36 (m, 1H), 3.93 (br. s., 3H), 4.31-4.41 (m, 2H), 4.48-4.65 (m, 3H), 6.89-7.02 (m, 1H), 7.78 (br. s., 1H), 7.84 (d, J=8.59 Hz, 1H), 8.20 (br. s., 1H), 10.84 (s, 1H). HRMS calculated for C24H31N4O5: 455.2294 (M+H). found (ESI, [M+H]+): 455.2311.

Workup

  1. extractionextracted with DCM (100 mL)
  2. washthe combined organic layers were washed with saturated aqueous NaHCO3 solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide crude product
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1d95aed36a234c6bbf6504495c9a314b
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes