Hydrochloric Acid → Isopropyl 3-[1-(3-{[bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenylcarbamate

HRID 2213512Notes

Reaction equation

HRID 2213512 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[C:31]([NH:35][C:36](=[O:41])[O:37][CH:38]([CH3:40])[CH3:39])[CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1.Cl>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:30]=[C:31]([NH:35][C:36](=[O:41])[O:37][CH:38]([CH3:39])[CH3:40])[CH:32]=[CH:33][CH:34]=3)[CH2:25][CH2:24]2)=[O:11])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 135116842,2-Bis(4-fluorophenyl)acetic acidHCID 21957208Isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate

Product 1

HCID 21957181Isopropyl 3-[1-(3-{[bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenylcarbamate

Procedure

Example 146 was prepared from bis(4-fluorophenyl)acetic acid and isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.43 (s, 2H), 7.30–7.19 (m, 4H), 7.11–7.07 (m, 1H), 7.01–6.96 (m, 5H), 6.88 (d, 1H, J=7.7 Hz), 6.69 (s, 1H), 4.97 (septet, 1H, J=6.3 Hz), 4.79 (s, 1H), 4.11 (q, 1H, J=6.8 Hz), 3.39 (q, 2H, J=5.6 Hz), 2.98–2.92 (m, 2H), 2.52–2.40 (m, 3H), 1.98 (t, 2H, J=11.5 Hz), 1.85–1.78 (m, 2H), 1.72–1.54 (m, 3H), 1.27 (d, 6H, J=6.3 Hz); ESMS m/e: 550.3 (M+H)+; Anal. Calc. for C32H37F2N3O3.0.87 HCl: C, 66.84; H, 6.61; N, 7.31.Found: C, 66.83; H, 6.48; N, 7.31.

Sources & evidence

ORD record
ord-06518eaf4d53438e85ae034f8b05ed2f
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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