4-Fluoroaniline → HCID 11634892, compound

HRID 1985649Notes

Reaction equation

HRID 1985649 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O:11][C:12]([C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:39])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]([F:38])([F:37])[F:36])[CH2:24][CH2:23]3)=[N:18][N:17]2[CH:40]=1)=O)C>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12]([C:14]2[N:15]=[C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:23][CH2:24][N:25]([C:28](=[O:39])[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[C:35]([F:36])([F:38])[F:37])[CH2:26][CH2:27]4)=[N:18][N:17]3[CH:40]=2)=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 66863489HCID 66863489, compound

Product 1

HCID 11634892HCID 11634892, compoundYield 57%

Procedure

Following the procedure as described in Example 1, making variations only as required to 4-fluoroaniline in place of isoamylamine to react with 6-[4-(2-trifluoromethyl-benzoyl)piperazin-1-yl]imidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid in 57% yield (0.065 g). m.p. 115-117° C. 1H NMR (300 MHz, CDCl3) δ 9.1 (s, 1H), 8.22 (s, 1H), 7.74-7.5 (m, 6H), 7.35-7.33 (m, 1H), 7.08-6.95 (m, 2H), 6.9 (d, J=7.6 Hz, 1H), 4.06-3.94 (m, 1H), 3.93-3.81 (m, 1H), 3.7-3.53 (m, 2H), 3.51-3.4 (m, 2H), 3.6-3.27 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 160.8, 160.2, 157.6, 154.9, 137.8, 135.7, 134.3, 134.2, 134.1, 134.0, 132.4, 129.5, 127.2, 126.9, 126.8, 126.7, 126.5, 125.4, 121.2, 121.1, 118.7, 115.8, 115.5, 112.2, 46.2, 46.1, 45.6, 41.2. MS (ES+) m/z 513.3 (M+1).

Sources & evidence

ORD record
ord-7c51af40c45348f1b128e84e66e14b67
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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