1-(p-Chlorophenyl)cyclopropanecarboxylic acid → HCID 21957213, compound

HRID 1269225Notes

Reaction equation

HRID 1269225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:25]=[CH:26][C:27]([F:36])=[C:28]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:29]=2)[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([F:36])=[C:28]([NH:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH:29]=4)[CH2:20][CH2:19]3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 21957269HCID 21957269, compound

Product 1

HCID 21957213HCID 21957213, compound

Procedure

Example 47 was prepared from 1-(4-chlorophenyl)cyclopropanecarboxylic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 8.32–8.18 (m, 1H), 7.43–7.25 (m, 5H), 7.08–6.93 (m, 1H), 6.93–6.79 (br, 1H), 5.74–5.59 (br, 1H), 3.35–3.15 (m, 2H), 3.93–2.75 (m, 2H), 2.65–2.49 (m, 1H), 2.49–2.34 (m, 1H), 2.34–2.19 (m, 2H), 2.00–1.83 (m, 2H), 1.82–1.68 (m, 2H), 1.68–1.48 (m, 4H), 1.36–1.17 (m, 2H), 1.27 (d, 6H, J=6.8 Hz), 1.0 (s, 2H); ESMS m/e: 500.3 (M+H)+; Anal. Calc. for (HCl salt) C28H36Cl2FN3O2.0.45CHCl3: C, 57.85; H, 6.22; N, 7.11. Found: C, 57.61; H, 6.37; N, 7.30.

Sources & evidence

ORD record
ord-b158a024089848669f5dff3d822c8f44
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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