Pentylamine → HCID 11598315, compound

HRID 1985645Notes

Reaction equation

[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].C([O:9][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:35])[F:34])[CH2:22][CH2:21]3)=[N:16][N:15]2[CH:38]=1)=O)C>>[CH2:1]([NH:6][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:34])([F:36])[F:35])[CH2:24][CH2:25]3)=[N:16][N:15]2[CH:38]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Reactant 2

HCID 8060Pentylamine

HCID 66863489HCID 66863489, compound

Product 1

HCID 11598315HCID 11598315, compoundYield 56%

Procedure

Following the procedure as described in Example 1, making variations only as required to use n-pentylamine 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 56% yield (0.062 g). m.p. 179-180° C. 1H NMR (300 MHz, CDCl3) δ 8.14 (s, 1H), 7.75-7.5 (m, 4H), 7.38-7.27 (s, 2H), 6.89 (d, J=9.6 Hz, 1H), 4.07-3.8 (m, 2H), 3.7-3.51 (m, 2H), 3.5-3.28 (m, 6H), 1.68-1.52 (m, 2H), 1.45-1.28 (m, 4H), 0.89 (t, J=2.1 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 162.3, 154.8, 138.2, 134.3, 134.2, 132.4, 129.5, 127.1, 126.8, 126.8, 126.2, 125.4, 121.8, 118.2, 111.9, 46.2, 41.2, 39.1, 29.4, 29.1, 22.4, 13.9. MS (ES+) m/z 489.2 (M+1).

Sources & evidence

ORD record: ord-b1d28ab68d8644bf8f7c217cf2b98c2d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547698B2

Reaction notes

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