Dimethylamine → HCID 9867673, compound

HRID 2300897Notes

Reaction equation

[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[N:26]=[N:27][C:28](Cl)=[CH:29][CH:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][NH:33][CH3:34]>C(O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[N:26]=[N:27][C:28]([N:33]([CH3:34])[CH3:32])=[CH:29][CH:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-[(S)-1-phenylethylamino]-4-[5-(6-chloropyridazin-3-yl)benzimidazol-1-yl]pyrimidine (13.2 mg) was mixed with 33% dimethylamine in ethanol (1 mL) in a sealed tube, the system heated to 60° C. for 15 h. The mixture was cooled, concentrated and the residue purified on silica gel (2.5%MeOH in CH2Cl2) to yield 11.2 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.51 (br s, 1H); 8.41 (d, J=5.5 Hz, 1H); 8.27 (s, 1H); 8.19 (br s, 1H); 7.89 (br s, 1H); 7.73 (d, J=9.6 Hz, 1H); 7.46 (m, 2H); 7.41 (t, J=7.5 Hz, 2H); 7.30 (m, 1H); 6.93 (d, J=1H); 6.81 (d, J=5.5 Hz, 1H); 5.80 (br s, 1H); 5.22 (br s, 1H); 3.26 (s, 6H); 1.65 (d, J=6.9 Hz, 3H). Mass spectrum (ESI) 437.4 (M+1).

Workup

temperatureThe mixture was cooled
concentrationconcentrated
customthe residue purified on silica gel (2.5%MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-81b62ebb45bb485d84bc2ad4615b39b1
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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