N'-(2,4-difluorophenyl)butane-1,4-diamine → HCID 59254956, compound

HRID 639483Notes

Reaction equation

CS(O[CH2:6][CH2:7][N:8]1[C:16]2[N:15]=[C:14]([NH2:17])[N:13]3[N:18]=[C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[C:12]3[C:11]=2[CH:10]=[CH:9]1)(=O)=O.[F:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[NH:34][CH2:35][CH2:36][CH2:37][CH2:38][NH2:39]>C(O)CCC.CN(C=O)C.C1CCN2C(=NCCC2)CC1>[NH2:17][C:14]1[N:13]2[N:18]=[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:12]2[C:11]2[CH:10]=[CH:9][N:8]([CH2:7][CH2:6][NH:39][CH2:38][CH2:37][CH2:36][CH2:35][NH:34][C:28]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=3[F:26])[C:16]=2[N:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The title D compound of Example 1, 2-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethyl methanesulfonate (20 mg, 0.06 mmol) and the title A compound, N′-(2,4-difluorophenyl)butane-1,4-diamine (22 mg, 0.12 mmol) are dissolved in 1 mL of n-butanol/DMF (1:1), to which solution is added 8 drops of DBU. The solution is heated at 110° C. for 1 h. The reaction is complete as indicated by TLC. The solvent is removed under vacuum and the residue is purified by flash chromatography to obtain N1-(2-(5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)-N4-(2,4-difluorophenyl)butane-1,4-diamine as an off-white solid: 1H NMR (CDCl3) 51.51-1.68 (m, 4H), 2.7 (t, 2H, J=6.81 Hz), 3.04-3.10 (m, 4H), 4.29 (t, 2H, J=6.05 Hz), 6.50-6.57 (m, 1H), 6.58 (dd, 1H, J=3.44, 1.73 Hz), 6.66-6.78 (m, 2H), 6.80 (d, 1H, J=3.47 Hz), 6.91 (s, 1H), 7.24 (dd, 1H, J=3.44, 0.76 Hz), 7.61 (dd, 1H, J=1.73, 0.76 Hz).

Workup

customThe solvent is removed under vacuum
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-2d3c31ab12bf418ca323656848443ae4
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691869B2

Reaction notes

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