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Triethylamine → HCID 10410368, compound

HRID 1435880
Notes
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Reaction equation

HRID 1435880 reaction equation
Cl.[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH2:22])=[N:18][CH:19]=1.C(N(CC)CC)C.[O:30]1[C:39]2[CH:38]=[C:37]([CH:40]=O)[N:36]=[CH:35][C:34]=2[O:33][CH2:32][CH2:31]1.[BH4-].[Na+]>C(Cl)Cl.CCO>[O:30]1[C:39]2[CH:38]=[C:37]([CH2:40][NH:22][CH2:21][CH2:20][C:17]3[CH:16]=[CH:15][C:14]([C:7]4[C:6]5[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH3:2])[N:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:19][N:18]=3)[N:36]=[CH:35][C:34]=2[O:33][CH2:32][CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 68441439(2-{5-[6-(Methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)amine hydrochloride salt

Product 1

HCID 10410368HCID 10410368, compoundYield 168.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-{5-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)amine hydrochloride salt (0.69 mmole) in dry CH2Cl2 (25 mL) and dry EtOH (10 mL) at RT was added triethylamine (0.29 mL, 2.07 mmole) and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (0.12 g, 0.73 mmole). After 24 h, the reaction contents were concentrated and dried under high vacuum. To a stirred solution of the crude imine in dry EtOH (25 mL) at RT was added NaBH4 (0.03 g, 0.73 mmole). After 24 h, Silica gel (5 g) was added to the reaction solution and the suspension was concentrated under vacuum to a dry solid. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.50 g, 72%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.52 (d, J=1.8 Hz, 1H), 9.22 (d, J=5.6 Hz, 1H), 9.02 (d, J=8.3 Hz; 1H), 8.57 (m, 2H), 8.48 (d, J=5.6 Hz, 1H), 8.19 (d, J=9.3 Hz, 1H), 7.79 (s, 1H), 7.68 (d, J=9.3 Hz, 1H), 4.66 (m, 4H), 4.54 (s, 2H), 4.13 (s, 3H), 3.82 (m, 2H), 3.71 (s, 2H). LC-MS (ES) m/e 430 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated
  3. customdried under high vacuum
  4. waitAfter 24 h
  5. additionSilica gel (5 g) was added to the reaction solution
  6. concentrationthe suspension was concentrated under vacuum to a dry solid
  7. customPurification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-d71b24495a334c9e82d2e4bb0c87e561
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07618959B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes