Formaldehyde → HCID 58574200, compound

HRID 1619424Notes

Reaction equation

HRID 1619424 reaction equation
C=O.[CH3:3][C:4]1[S:8][C:7]([NH:9][C:10]([C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:28])[N:17]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:18]4=[N:19]3)=[CH:14][CH:13]=2)=[O:11])=[N:6][CH:5]=1.[CH3:29]C([O-])=O.[Na+]>CC(O)=O.O>[CH2:29]=[C:22]1[C:18]2=[N:19][C:20]3[C:15]([C:16](=[O:28])[N:17]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[CH:14][CH:13]=[C:12]([C:10]([NH:9][C:7]1[S:8][C:4]([CH3:3])=[CH:5][N:6]=1)=[O:11])[CH:21]=3

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 17457030HCID 17457030, compound

Product 1

HCID 58574200HCID 58574200, compoundYield 144%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Paraformaldehyde (10 mg), N-(5-methylthiazol-2-yl)-13-oxo-7,8,9,10,11,13-hexahydro-6H-azocino[2,1-b]quinazoline-3-carboxamide (60 mg, 0.16 mmol) and NaOAc (3 mg, 0.0365 mmol) in 5 mL HOAc was stirred at 120° C. overnight in a sealed tube. The completion was monitored by TLC and LC-MS. The sealed tube was then placed in water until cool. The suspension was diluted with water (30 mL) and adjusted pH to 8, then extracted with ethyl acetate (3×50 mL). The organic phase was concentrated to give crude product and 20 mg of the desired product was obtained by column chromatography. MS (ESI): 381 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.45-8.42 (d, J=8.22 Hz, 1H), 8.27 (s, 1H), 8.04-8.00 (dd, J=8.39, 1.61 Hz, 1H), 7.28 (s, 2H), 5.52 (s, 1H), 5.30 (s, 1H), 4.39-4.33 (m, 2H). 2.72-2.59 (m, 2H), 2.42 (s, 3H), 1.96-1.88 (m, 2H), 1.72-1.68 (m, 2H), 1.56-1.51 (m, 2H).

Workup

  1. temperatureuntil cool
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. concentrationThe organic phase was concentrated
  4. customto give crude product

Sources & evidence

ORD record
ord-61a20e030e1f4349936090ccbf55cf83
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…