Formaldehyde → HCID 53391360, compound

HRID 1045754Notes

Reaction equation

HRID 1045754 reaction equation
[N:1]1([C:7]2[C:8]3[N:9]([CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:20]=3)[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:26]O.C=O>C(Cl)Cl>[CH3:26][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:8]3[N:9]([CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:20]=3)[C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][N:12]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 887MethanolHCID 53390240HCID 53390240, compound

Product 1

HCID 53391360HCID 53391360, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 25 mL round bottom flask was charged with ethyl 8-(piperazin-1-yl)-5-(thiophen-2-yl)imidazo[1,2-a]pyrazine-2-carboxylate (200 mg, 0.56 mmol), MeOH (15 mL), CH2Cl2 (15 mL), 40% aqueous formaldehyde (1 mL) and NaBH3(CN) (250 mg, 3.9 mmol). The mixture was stirred at 25° C. for 1 h. Reaction progress was monitored by LC-MS. Work-up: the solvent was evaporated. The residue was purified by flash column chromatography on silica gel with a 1:20 MeOH/CH2Cl2, to afford 150 mg (72%) of the product. 1H NMR (300 MHz, CDCl3) δ: 8.33 (s, 1H), 7.50 (s, 1H), 7.48 (dd, J=5.4, 1.2 Hz, 1H), 7.35 (dd, J=3.3, 1.2 Hz, 1H), 7.20 (dd, J=5.4, 3.3 Hz, 1H), 4.43-4.38 (m, 6H), 2.59 (t, J=5.1 Hz, 4H), 1.40 (t, J=6.9 Hz, 3H). MS m/z: 372 (M+H+).

Workup

  1. customReaction progress
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash column chromatography on silica gel with a 1:20 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d911d5184bfb4593bbd9c190dab3ef96
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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