Benzilic acid → HCID 58840920, compound

HRID 1269325Notes

Reaction equation

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

Participants

Reactant 2

HCID 6463Benzilic acid

HCID 16757466N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide

Product 1

HCID 58840920HCID 58840920, compound

Procedure

Example 155 was prepared from hydroxy(diphenyl)acetic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 8.96 (s, 1 H), 8.39 (t, 1 H, J=8.4 Hz), 7.62–7.45 (m, 4 H), 7.38–7.18 (m, 7 H), 6.85–6.74 (m, 1 H), 5.43–5.14 (br, 1 H), 3.59–3.39 (m, 2 H), 3.11–2.97 (m, 2 H), 2.97–2.79 (m, 1 H), 2.59–2.45 (m, 2 H), 2.45–2.29 (m, 1 H), 2.14–1.86 (m, 4 H), 1.81–1.56 (m, 4 H), 1.01 (d, 6 H, J=7.2 Hz); ESMS m/e: 550.4 (M+H)+.

Sources & evidence

ORD record: ord-c52d8f18eb8042a8b3f047f8245f2975
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199135B2

Reaction notes

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