Diethyl Ether → HCID 69588553, compound

HRID 859138Notes

Reaction equation

HRID 859138 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:25][CH3:26])[C:17]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])=[C:13]2[CH:12]=[CH:11][CH:10]=1.[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].CCOCC.CCCCCC>C(OCC)(=O)C.CO>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:25][CH3:26])[C:17]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 444266Maleic AcidHCID 21984682HCID 21984682, compound

Product 1

HCID 69588553HCID 69588553, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-(2,4-dichlorophenyl)-2-ethyl-N,N-dipropylpyrazolo[1,5-a]pyridin-3-amine (530 mg, 1.4 mmol) in ethyl acetate (20 mL) was treated with maleic acid (169 mg, 1.4 mmol) dissolved in CH3OH (1.5 mL). The solution was stirred at room temperature for 1.5 hours then concentrated in vacuo to give a yellow oil. Trituration with Et2O and hexane gave 560 mg (81%) of a brown solid as the title compound: mp 106–112° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.82 (d, J=1.9 Hz, 1H), 7.68–7.57 (m, 3H), 7.20–7.16 (m, 1H), 6.78 (d, J=6.4 Hz, 1H), 6.26 (s, 1H), 3.03 (t, J=7.0 Hz, 4H), 2.65 (q, J=7.5 Hz, 2H), 1.36–1.27 (m, 4H), 1.13 (t, J=7.5 Hz, 3H), 0.85 (t, J=7.3 Hz, 6H); 13C NMR (100 MHz, DMSO-d6) δ 166.6, 153.2, 136.3, 135.9, 134.6, 134.4, 133.2, 131.8, 130.5, 128.9, 127.4, 121.9, 116.6, 112.5, 57.4, 21.2, 19.0, 13.9, 11.4; IR (diffuse reflectance) 2975, 2965, 2940, 2491, 2353, 2335, 1983, 1948, 1586, 1552, 1547, 1485, 1470, 1455, 1354 cm−1; HRMS (FAB) calcd for C21H25Cl2N3+H 390.1504. found 390.1501; Anal. Calcd for C21H25Cl2N3.C4H4O4: C, 59.29; H, 5.77; N, 8.30. Found: C, 59.40; H, 5.78; N, 8.14.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give a yellow oil

Sources & evidence

ORD record
ord-64734ea1b6b641a289a92c2c223c4704
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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