3-(Pyrrolidin-1-ylmethyl)aniline → 6-(2-chlorophenyl)-2-{[3-(pyrrolidin-1-ylmethyl)phenyl]amino}imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

HRID 2370615Notes

Reaction equation

HRID 2370615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[N:25]1([CH2:30][C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:29][CH2:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:34][C:33]3[CH:35]=[CH:36][CH:37]=[C:31]([CH2:30][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)[CH:32]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

3

Reactant 2

HCID 10964073-(Pyrrolidin-1-ylmethyl)anilineHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 681944726-(2-chlorophenyl)-2-{[3-(pyrrolidin-1-ylmethyl)phenyl]amino}imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Procedure

A mixture of Example 1E (50.0 mg, 0.139 mmol) and 3-(pyrrolidin-1-ylmethyl)aniline (49.0 mg, 0.278 mmol) was heated in a capped vial at 110° C. for 1 hour. The crude material was purified by HPLC as described in Example 1F to provide the tile compound as a trifluoroacetic acid salt. 1H NMR (400 MHz, CD3OD) δ ppm 1.96-2.10 (m, 2H), 2.14-2.31 (m, 2H), 3.18-3.28 (m, 2H), 3.49-3.65 (m, 2H), 4.44 (s, 2H), 7.07 (d, J=1.83 Hz, 1H), 7.31 (d, J=7.32 Hz, 1H), 7.50-7.63 (m, 4H), 7.66-7.73 (m, 1H), 7.83-8.08 (m, 3H), 8.01 (s, 1H), 9.21 (s, 1H). MS (ESI+) m/z 472.2 (M+H)+.

Workup

  1. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-ee933b28bd0a4f5ab060824f7c563ab8
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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