Triethylamine → HCID 118036754, compound

HRID 1777983Notes

Reaction equation

HRID 1777983 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH:14]=O)=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.Cl.[NH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH2:14][N:19]2[CH2:20][CH2:21][CH2:22][C:23]2=[O:25])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 1180364262-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde2×

Product 1

HCID 118036754HCID 118036754, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 5.0 g, 17.99 mmol), methyl 4-aminobutanoate hydrochloride (4.14 g, 27.0 mmol) and triethylamine (4.24 ml, 30.6 mmol) in 1,2-dichloroethane (85 ml) at room temperature was stirred for 1.5 h and sodium triacetoxyborohydride (5.72 g, 27.0 mmol) added. The reaction mixture was stirred for 18 h at room temperature, partitioned between saturated aqueous NaHCO3 solution and DCM, extracted 2× with DCM, dried over Na2SO4 and evaporated. The residue was triturated with Et2O (20 ml) and filtered washing with Et2O to give the title compound as a pale brown solid.

Workup

  1. stirringThe reaction mixture was stirred for 18 h at room temperature
  2. custompartitioned between saturated aqueous NaHCO3 solution and DCM
  3. extractionextracted 2× with DCM
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was triturated with Et2O (20 ml)
  7. filtrationfiltered
  8. washwashing with Et2O

Sources & evidence

ORD record
ord-994d442d062249d18114e215f268a409
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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