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Hydrochloric Acid → 3-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-hydroxy-3-cyclobuten-3-yl)amino-1H-indole

HRID 441086
Notes
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Reaction equation

HRID 441086 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28]5[C:29](=[O:37])[C:30](=[O:36])[C:31]=5[O:32]C(C)C)[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1.Cl.O>CO>[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28]5[C:31](=[O:32])[C:30](=[O:36])[C:29]=5[OH:37])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 224056883-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-[1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]amino-1H-indole

Product 1

HCID 224057103-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-hydroxy-3-cyclobuten-3-yl)amino-1H-indoleYield 46.3%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5 [1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]aminoindole (I-3) (0.175 g, 0.35 mmol) in 5 mL of methanol was added 0.10 mL (0.60 mmol) of 6N HCl and the mixture was heated at ca. 80° C. for 5 h. Another 0.10 mL (0.60 mmol) of 6N HCl was then added, as well as 0.20 mL of H2O, and the mixture was heated at ca. 100° C. for 18 h. On cooling to room temperature, the resulting suspension was filtered and the residue was washed (acetone, ether) and then air-dried. This solid (0.130 g) was taken up in methanol and the resulting solution was treated with charcoal, filtered and evaporated to give the hydrochloride salt of the title compound (0.075 g, 36%) as a beige solid, mp 215° C. (dec): IR (KBr) 3410 (br), 3240 (br), 1783, 1700, 1632, 1547 cm -1 ; 1H NMR (DMSO-d6, 200 MHz) δ10.88 (s, 1H), 10.37 (s, 1H), 8.56 (s, 1H), 8.19 (s, 1H), 7.62 (s, 1H), 7.29 (d, J=8.6 Hz, 1H), 7.21 (s, 1H), 7.10 (dd, J=8.6, 1.8 Hz, 1H), 4.80 (br m, 2H), 3.90 (s, 3H), 3.57 (br m, 4H), 3.13 (br m, 4H), 2.73 (m, 2H), 2.12 (m, 2H). Anal. Calcd for C24H26N6O4. 3 HCl. H2O: C, 48.86; H, 5.30; N, 14.25. Found: C, 48.81; H, 5.51; N, 14.22.

Workup

  1. temperatureOn cooling to room temperature
  2. filtrationthe resulting suspension was filtered
  3. washthe residue was washed (acetone, ether)
  4. customair-dried
  5. additionthe resulting solution was treated with charcoal
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e1c4f15dee3c450093edc9e018a50689
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05521188

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes