Hydrochloric Acid → HCID 58346509, compound

HRID 222061Notes

Reaction equation

HRID 222061 reaction equation
Cl[C:2]1[N:14]=[CH:13][N:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][C:7]3[N:17]([CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)[N:16]=[CH:15][C:8]=3[C:9]=1[S:10]2.Cl.[O:28]1[CH2:33][CH2:32]OCC1>C(O)(C)C>[CH3:4][C:5]1[CH:6]=[C:7]([NH:17][C:2]2[C:3]3[C:4]4[CH2:5][CH2:6][C:7]5[N:17]([CH2:18][CH2:19][N:20]6[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]6)[N:16]=[CH:15][C:8]=5[C:9]=4[S:10][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:8]=[CH:32][C:33]=1[OH:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86655313HCID 86655313, compound

Product 1

HCID 58346509HCID 58346509, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 6-chloro-3-[2-(4-methyl-piperazin-1-yl)-ethyl]-4,5-dihydro-3H-10-thia-2,3,7,9-tetraaza-cyclopenta[a]fluorene (150 mg, 0.39 mmol) and 4-amino-O-cresol (71 mg, 0.58 mmol) in isopropanol (5 mL) was added 4M HCl in dioxane (0.67 mL, 2.7 mmol). The reaction mixture was sealed in a microwave reaction vessel and it was placed in a microwave instrument at 160° C. for 10 min. After it was cooled to room temperature, solvents were evaporated and the residue was dissolved in MeOH/water/DMF and purified by prep. HPLC. After drying, the TFA salt was neutralized with saturated NaHCO3 and extracted with a mixture of CHCl3:isopropanol (v/v, 3:1). The organic phase was dried over Na2SO4 and concentrated to dryness. The desired product was obtained as a pale solid (174 mg, 95%). 1H-NMR (CD2Cl2-d2) δ 8.34 (s, 1H), 7.55 (s, 1H), 7.28 (m, 2H), 6.88 (b, 1H), 6.80 (m, 1H), 4.20 (t, 2H, J=6.2 Hz), 3.38 (t, 2H, J=8.3 Hz), 3.13 (t, 2H, J=8.4 Hz), 2.85 (t, 2H, J=6.2 Hz), 2.62-2.45 (b, 8H), 2.30 (s, 3H), 2.26 (s, 3H); LCMS RT=1.89 min; [M+H]+=476.2.

Workup

  1. customThe reaction mixture was sealed in a microwave reaction vessel and it
  2. customsolvents were evaporated
  3. dissolutionthe residue was dissolved in MeOH/water/DMF
  4. custompurified by prep
  5. customAfter drying
  6. extractionextracted with a mixture of CHCl3
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-46601dc53843425a95d3a16643a94abb
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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