Hydrochloric Acid → HCID 11706051, compound

HRID 639108Notes

Reaction equation

HRID 639108 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([CH3:25])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:23]#[N:24])[CH2:5]1.[O:26]=[C:27]1[CH2:32][S:31][C:30]2[CH:33]=[CH:34][C:35]([CH:37]=O)=[N:36][C:29]=2[NH:28]1>CO.C(Cl)Cl>[CH3:25][C:4]1([CH2:3][NH:2][CH2:37][C:35]2[CH:34]=[CH:33][C:30]3[S:31][CH2:32][C:27](=[O:26])[NH:28][C:29]=3[N:36]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:23]#[N:24])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 115935913-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehydeHCID 59026101HCID 59026101, compound

Product 1

HCID 11706051HCID 11706051, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the HCl salt of 4-{2-[3-(aminomethyl)-3-methyl-1-pyrrolidinyl]ethyl}-6-(methyloxy)-3-quinolinecarbonitrile (50 mg) in MeOH (2 mL) and DCM (2 mL) were added NaHCO (130 mg, 1.6 mmol) followed by 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde (30 mg, 0.18 mmol). After 24 h at 25° C., NaBH (10 mg, 0.27 mmol) was added. After 1 h, the reaction was concentrated and the residue was partitioned between DCM-H O. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried over MgSO, concentrated and purified via column chromatography (silica, 4% MeOH in DCM (1% NH OH)) yielding the title compound (20 mg) as a brown oil: LC/MS (ES) m/e 503 (M+H) 1H NMR (CDCl3, 400 MHz) δ 8.85 (s, 1H), 8.22 (d, J=9.0 Hz, 1H), 7.58 (d, J=7.8 Hz, 1H), 7.55 (d, J=9.0 Hz, 1H), 7.35 (s, 1H), 6.95 (d, J=7.8 Hz, 1H), 4.12 (s, 3H), 3.83 (s, 2H), 3.51 (m, 3H), 2.9-2.5 (m, 6H), 2.3 (m, 1H), 1.85 (m, 1H), 1.55 (m, 1H), 1.1 (s, 3H).

Workup

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated
  3. customthe residue was partitioned between DCM-H O
  4. extractionThe aqueous phase was extracted several times with DCM
  5. dry with materialthe combined organic fractions were dried over MgSO
  6. concentrationconcentrated
  7. custompurified via column chromatography (silica, 4% MeOH in DCM (1% NH OH))

Sources & evidence

ORD record
ord-1bb0e4186f284843ae50d89fdbf01072
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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