3-Cyclopentylpropionyl chloride → HCID 57841331, compound

HRID 733624Notes

Reaction equation

HRID 733624 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:31]=[CH:30][C:13]([CH2:14][NH:15][CH:16]3[C:25]4[CH:24]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:21][C:20]=4[CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:32]1([CH2:37][CH2:38][C:39](Cl)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:37][CH2:38][C:39]([N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([C:9]#[C:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:31][CH:30]=2)[CH:16]2[C:25]3[CH:24]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18][CH2:17]2)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 11373316HCID 11373316, compound

Product 1

HCID 57841331HCID 57841331, compound

Procedure

The titled compound was prepared following the procedure B using methyl 8-({4-[(4-fluorophenyl)ethynyl]benzyl}amino)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate and 3-cyclopentylpropionyl chloride as a white powder (80%). 1H NMR (CDCl3, 300 MHz) δ 1.06 (m, 2H), 1.41-2.10 (m, 11H), 2.27-2.60 (m, 2H), 2.77 (m, 2H), 3.87 (s, 3.4H), 4.07 (d, J=17.9 Hz, 0.6H), 4.52 (d, J=18.5 Hz, 0.6H), 4.86 (d, J=15.6 Hz, 0.4H), 5.10 (m, 0.4H), 6.06 (m, 0.6H), 7.00-7.20 (m, 5H), 7.36 (d, J=8.1 Hz, 1H), 7.48 (m, 3H), 7.66 (d, J=10.4 Hz, 1H), 7.78 (m, 1H). HPLC, Rt: 5.83 min (Purity: 99.4%).

Sources & evidence

ORD record
ord-0c07e9a9db6a4c9ea49f6e987753fa1d
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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