Ammonia → HCID 57933083, compound

HRID 1432683Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])=[C:5]([Br:7])[N:6]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[Cs+].[Cs+].N>CO.CCOC(C)=O.CCCCCC.C1COCC1>[Br:7][C:5]1[N:6]=[C:2]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[S:3][C:4]=1[C:8]1[N:12]2[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]2=[N:10][C:9]=1[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

100 mg (0.22 mmol) of 3-(2,4-Dibromo-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.22 mmol), 96 mg of morpholine (1.1 mmol) and 215 mg of Cs2CO3 (0.66 mmol) are put in a 4 ml vial with dry THF, and the vial is capped with a Teflon cap. The vial is heated at 120° C. for overnight. The reaction mixture is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=9:3:1) to give 72.7 mg of the title compound. Yield 71%. mass spectrum (m/e): 465 (M+1); 1H-NMR (CDCl3): 6.73 (s, 1H), 3.87 (t, 4H, J=5.1 Hz), 3.58 (t, 4H, J=5.1 Hz), 3.35 (m, 1H), 2.57 (s, 3H), 2.53 (s, 3H), 1.86 (m, 4H), 0.90 (t, 6H, J=7.5 Hz).

Workup

customcap

Sources & evidence

ORD record: ord-8a020ade54a44c77941549ec14cfc349
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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