2-Amino-5-chloropyridine → HCID 11642251, compound

HRID 1985647Notes

Reaction equation

HRID 1985647 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=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>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][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])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 66863489HCID 66863489, compound

Product 1

HCID 11642251HCID 11642251, compoundYield 24%

Procedure

Following the procedure as described in Example 1, making variations only as required to 5-chloropyridin-2-ylamine 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 24% yield (0.028 g). m.p. 265-268° C. 1H NMR (300 MHz, CDCl3) δ 9.78 (s, 1H), 8.35 (d, J=7.6 Hz, 1H), 8.27-8.25 (2H), 7.81-7.52 (m, 5H), 7.42-7.31 (m, 1H), 6.92 (d, J=7.6 Hz, 1H), 6.9 (d, J=7.6 Hz, 1H), 4.08-3.97 (m, 1H), 3.95-3.83 (m, 1H), 3.72-3.55 (m, 2H), 3.53-3.43 (m, 2H), 3.37-3.27 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 160.7, 154.9, 149.7, 146.7, 137.8, 137.3, 135.8, 134.2, 132.4, 129.5, 127.2, 127.2, 126.9, 126.8, 126.7, 126.5, 125.4, 118.9, 114.5, 112.3, 46.2, 46.18, 45.6, 41.2. MS (ES+) m/z 530.1 (M+1).

Sources & evidence

ORD record
ord-a89a1526ad9047e8aa92e582a772fa11
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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