N-BOC-ethylenediamine → 2-[2-(N-tert-butoxycarbonylamino)ethyl]-5-[[2-(N-tert-butoxycarbonylamino)ethyl]amino]isoquino[8,7,6-cd]indazole-6(2H)-one

HRID 1451486Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][C:16](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:15]3[C:31](=[O:38])[C:32]4[CH:33]=[CH:34][N:35]=[CH:36][C:37]=4[C:13]([C:14]=23)=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][NH2:49])=[O:45])([CH3:42])([CH3:41])[CH3:40]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][C:16]([NH:49][CH2:48][CH2:47][NH:46][C:44]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:45])=[C:15]3[C:31](=[O:38])[C:32]4[CH:33]=[CH:34][N:35]=[CH:36][C:37]=4[C:13]([C:14]=23)=[N:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one of Example 3 (0.535 g) and N-(tert-butoxycarbonyl)ethylenediamine (prepared according to Synt. Comm., 20, 2559, (1990); 1.12 g) in dry pyridine (5.35 mL) is heated at 80° C. The dark solution obtained is held at this temperature for 5 hours, then it is concentrated to dryness and partitioned between brine (30 mL) and ethyl acetate (2×25 mL). The orange-red solid insoluble in the biphasic mixture is separated by suction filtration and dried at 40° C. under vacuum (0.43 g).

Workup

customThe dark solution obtained
concentrationit is concentrated to dryness
custompartitioned between brine (30 mL) and ethyl acetate (2×25 mL)
customThe orange-red solid insoluble in the biphasic mixture is separated by suction filtration
customdried at 40° C. under vacuum (0.43 g)

Sources & evidence

ORD record: ord-1a889f0b0701441e9b13915a5f554767
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604246

Reaction notes

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