4-Fluorobenzylamine → HCID 11699332, compound

HRID 1985648Notes

Reaction equation

HRID 1985648 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:12][C:13]([C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:40])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])[CH2:25][CH2:24]3)=[N:19][N:18]2[CH:41]=1)=O)C>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:13]([C:15]2[N:16]=[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:24][CH2:25][N:26]([C:29](=[O:40])[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[C:36]([F:37])([F:39])[F:38])[CH2:27][CH2:28]4)=[N:19][N:18]3[CH:41]=2)=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 66863489HCID 66863489, compound

Product 1

HCID 11699332HCID 11699332, compoundYield 30%

Procedure

Following the procedure as described in Example 1, making variations only as required to 4-fluorobenzylamine in place of isoamylamine to react with 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]imidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid in 30% yield (0.035 g). m.p. 205-207° C. 1H NMR (300 MHz, CDCl3) δ 8.18 (s, 1H), 7.77-7.5 (m, 5H), 7.38-7.27 (m, 3H), 7.03-6.94 (m, 2H), 6.9 (d, J=9.6 Hz, 1H), 4.58 (d, J=6 Hz, 2H), 4.06-3.94 (m, 1H), 3.93-3.81 (m, 1H), 3.69-3.54 (m, 2H), 3.52-3.42 (m, 2H), 3.36-3.27 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 163.7, 162.3, 160.5, 154.8, 137.8, 135.7, 134.2, 132.4, 129.6, 129.5, 126.9, 126.8, 126.7, 125.3, 124.4, 121.8, 118.4, 115.6, 115.3, 112.0, 46.2, 46.2, 45.6, 42.4, 41.2. MS (ES+) m/z 527.2 (M+1).

Sources & evidence

ORD record
ord-f7450ff4376c41d6a7196a19269c65a6
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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