Triethylamine → HCID 59262198, compound

HRID 906378Notes

Reaction equation

HRID 906378 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[N:7][CH:8]=1.COC(OC)C1N=CC(NC)=CC=1.[CH3:24][C@H:25]1[CH2:30][NH:29][CH2:28][CH2:27][N:26]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH3:24][C@H:25]1[CH2:30][N:29]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][CH3:1])=[CH:8][N:7]=2)[CH2:28][CH2:27][N:26]1[C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 55287558HCID 55287558, compoundHCID 59262119HCID 59262119, compound

Product 1

HCID 59262198HCID 59262198, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(methylamino)-2-pyridinecarbaldehyde and 6-[bis(methyloxy)methyl]-N-methyl-3-pyridinamine (D60) (0.622 g), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.910 g, 4.552 mmol) and triethylamine (0.418 g, 4.139 mmol) in 1,2-DCE (40 mL) was stirred at room temperature overnight. Sodium tri(acetoxy)borohydride (1.14 g, 5.38 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was diluted with DCM and washed with saturated aq. NaHCO3 solution and water. The organic layer was dried and concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% EtOAc/petroleum ether gave the title compound as a yellow/brown oil (0.542 g). δH (CDCl3, 400 MHz) 7.96 (1H, d), 7.23 (1H, d), 6.88 (1H, dd), 4.17 (1H, br.s), 3.80 (2H, d), 3.58 (1H, d), 3.45 (1H, d), 3.12 (1H, td), 2.86 (3H, s), 2.76 (1H, m), 2.58 (1H, m), 2.18 (1H, dd), 2.07 (1H, m), 1.45 (9H, s), 1.23 (3H, d). MS (ES): MH+ 321.4

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. washwashed with saturated aq. NaHCO3 solution and water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography
  7. washElution with 0-100% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-d7739547bb494ca184ad2c18d3c0084e
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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