Triethylamine → HCID 24784185, compound

HRID 2233344Notes

Reaction equation

HRID 2233344 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[O:19][C:18](=[O:21])[CH:17]=[CH:16]3)[CH2:5][CH2:4]1.CCN(CC)CC.[O:29]=[C:30]1[CH2:35][S:34][C:33]2[CH:36]=[CH:37][C:38]([CH:40]=O)=[N:39][C:32]=2[NH:31]1.[BH4-].[Na+]>CO.C(Cl)Cl>[O:21]=[C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[C:11]([CH2:10][CH2:9][N:6]3[CH2:7][CH2:8][CH:3]([NH:2][CH2:40][C:38]4[CH:37]=[CH:36][C:33]5[S:34][CH2:35][C:30](=[O:29])[NH:31][C:32]=5[N:39]=4)[CH2:4][CH2:5]3)[CH:12]=[CH:13][CH:14]=2)[O:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 86628019HCID 86628019, compound

Product 1

HCID 24784185HCID 24784185, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 8-[2-(4-amino-1-piperidinyl)ethyl]-2H-chromen-2-one hydrochloride (41 mg, 0.15 mmol), Et3N (0.10 mL), in 10% methanol/CH2Cl2 (5 mL) was added 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxaldehyde (32 mg, 0.17 mmol). The solution was allowed to stir at RT for 16 h, then sodium borohydride (7 mg, 0.17 mmol) was added. The solution was stirred for an additional 30 min then was concentrated under reduced pressure. Flash chromatography on silica gel (90:9:1 CHCl3/MeOH/conc NH4OH) gave the title compound (34 mg, 51%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, J=9.6 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.32 (m, 1H), 7.11 (d, J=7.8 Hz, 1H), 6.47 (d, J=9.6 Hz, 1H), 4.17 (s, 2H), 3.57 (s, 2H), 3.36-3.04 (m, 5H), 3.00-2.84 (m, 2H), 2.62-2.38 (m, 2H), 2.33-2.10 (m, 2H), 1.87-1.62 (m, 2H); MS (ES) m/e 451.1 (M+H)+.

Workup

  1. stirringThe solution was stirred for an additional 30 min
  2. concentrationthen was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee550c45de8a4e83a38887eb2f71cc47
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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