Pentylamine → HCID 11678612, compound

HRID 2074146Notes

Reaction equation

HRID 2074146 reaction equation
C[O:2][C:3]([C:5]1[N:9]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[N:8]=[C:7]([N:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])[CH2:22][CH2:21]2)[CH:6]=1)=O.[CH2:38]([NH2:43])[CH2:39][CH2:40][CH2:41][CH3:42].[C-]#N.[Na+]>>[CH2:13]([O:12][C:10]([N:9]1[C:5]([C:3](=[O:2])[NH:43][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:6][C:7]([N:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:34])([F:36])[F:35])[CH2:22][CH2:21]2)=[N:8]1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 8060PentylamineHCID 8929Sodium CyanideHCID 66584381HCID 66584381, compound

Product 1

HCID 11678612HCID 11678612, compoundYield 10%

Procedure

A mixture of above 3-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]-pyrazole-1,5-dicarboxylic acid 1-benzyl ester 5-methyl ester (0.800 g, ca. 1.5 mmol), amylamine (3.0 mL) and sodium cyanide (0.150 g, 3.0 mmol) was stirred at room temperature overnight and then purified by column chromatography to give the title compound (0.238 g, 10% in 2 steps). 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=7.5 Hz, 1H), 7.61-7.49 (m, 2H), 7.32 (d, J=7.5 Hz, 1H), 7.25-7.17 (m, 5H), 5.93-5.85 (m, 2H), 5.56 (s, 2H), 3.98-3.84 (m, 2H), 3.33-3.05 (m, 8H), 1.57-1.44 (m, 2H), 1.31-1.18 (m, 4H), 0.86 (t, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 167.4, 159.7, 157.0, 137.7, 136.3, 134.6, 132.2, 129.2, 128.3, 127.6, 127.4, 127.2, 127.1, 126.6, 126.2, 125.4, 92.2, 53.9, 48.1, 47.8, 46.4, 41.0, 39.5, 29.1, 28.9, 22.3, 13.9. MS (ES+) m/z 572.0 (M+1). m.p. 58-61° C.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-86862ff9d77e44cc9fc706e8a15f2cde
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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