Water → HCID 178439942, compound

HRID 274622Notes

Reaction equation

HRID 274622 reaction equation
[CH3:1][N:2]1[C:6]2[N:7]=[C:8]([CH2:47][CH2:48][CH3:49])[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:23]4[N:27](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:26]=[N:25][N:24]=4)=[CH:13][CH:12]=3)[C:5]=2[C:4]([CH3:50])=[N:3]1.O>CC(O)=O>[CH3:1][N:2]1[C:6]2[N:7]=[C:8]([CH2:47][CH2:48][CH3:49])[N:9]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:23]4[NH:24][N:25]=[N:26][N:27]=4)=[CH:15][CH:16]=3)[C:5]=2[C:4]([CH3:50])=[N:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 20093428HCID 20093428, compound

Product 1

HCID 178439942HCID 178439942, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The material prepared in Step E (160 mg, 0.24 mmol) was dissolved in glacial HOAc (2.0 mL) at 50° C. and H2O was added dropwise until the solution just became cloudy (approx. 0.7 mL). The mixture was kept at 50° C. for 2 hours and then was evaporated to dryness under a stream of nitrogen. The residue so formed was purified by preparative tlc on 1000μ SiO2 plates developed with CHCl3 /MeOH/NH4OH (80:20:2) to give 67 mg (68%) of the title compound as its ammonium salt. 1H NMR (200 MHz, DMSO-d6)δ 6.82-7.80 (m), 5.21 (s), 3.66 (s), 2.70 (t, J=9 Hz), 1.93 (s), 1.52-1.76 (m), 0.89 (t, J=9 Hz). FAB-MS: 413 (M+ +1). Anal. Calcd for C23H24N8 ·NH3 ·0.6 H2O; C, 62.74; H, 6.46; N, 28.63; Found: C, 62.49; H, 6.24; N, 28.73.

Workup

  1. customwas evaporated to dryness under a stream of nitrogen
  2. customThe residue so formed
  3. customwas purified by preparative tlc on 1000μ SiO2 plates

Sources & evidence

ORD record
ord-3c996b8adb3e469189b2ee9ebac6e46e
Source dataset
uspto-grants-1995_02
Patent number
US05389660

Reaction notes

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