HCID 10820771, compound → Bms-181885

HRID 441084Notes

Reaction equation

HRID 441084 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]([NH2:27])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1.CC([O:31][C:32]1[C:33](=[O:38])[C:34](=O)[C:35]=1[CH3:36])C>CN(C=O)C>[NH4+:5].[OH-:2].[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:34]5[C:33](=[O:38])[C:32](=[O:31])[C:35]=5[CH3:36])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 10820771HCID 10820771, compoundHCID 199620373-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-amino-1H-indole

Product 2

HCID 14923Ammonium HydroxideHCID 153988Bms-181885Yield 115.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-aminoindole (6) (0.190 g, 0.52 mmol) and 3-(1-methylethoxy)-4-methylcyclobut-3-ene-1,2-dione (3) (0.080 g, 0.52 mmol) in 1 mL of dry DMF was stirred at room temperature for 66 h and then it was heated at 130° C. (oil-bath temperature) for 6 h. The cooled mixture was evaporated and the residue was chromatographed (SiO2/CH2Cl2 --MeOH, 95:5 then CH2Cl2 --MeOH--NH4OH, 95:4.5:0.5 to 90:9:1) to give the title compound (0.138 g, 58%) as a brown foam. This material was treated with excess methanolic HCl, the resulting solution was evaporated and the residue was triturated with isopropanol to give the hydrochloride 0.140 g, 45%) as a solid, mp 200° C. (dec): IR (KBr) 3400, 3220, 1782, 1630, 1600 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.08-10.83 (m, 2H), 8.59 (s, 1H), 8.19 (s, 1H), 7.57-7.04 (m, 4H), 4.85 (m, 2H), 3.90 (s, 3H), 2.8-2.4 (m, 8H), 3,13 (m, 2H), 2.26 (s, 1.5H), 2.10 (m, 2H), 1.89 (s, 1.5H). Anal. Calcd for C25H28N6O3. 3 HCl 0.75 H2O. 0.25 C3H8O: C, 51.68; H, 5.81; N, 14.04. Found: C, 51.43; H, 5.61; N, 13.93.

Workup

  1. customThe cooled mixture was evaporated
  2. customthe residue was chromatographed (SiO2/CH2Cl2

Sources & evidence

ORD record
ord-94f40d964c4d4fdbaf2432a971a14cfe
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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