2,6-Dimethylbenzoic acid → HCID 57562986, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:13]2[CH:22]=[CH:21][C:16]3[O:17][CH2:18][CH2:19][O:20][C:15]=3[CH:14]=2)[CH2:8][CH2:7]1)[CH3:5].[CH3:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:34]=1[C:35](O)=[O:36]>>[Cl:30][C:28]1[CH:27]=[CH:26][C:25]([F:31])=[C:24]([CH:29]=1)[CH2:23][N:12]([C:13]1[CH:22]=[CH:21][C:16]2[O:17][CH2:18][CH2:19][O:20][C:15]=2[CH:14]=1)[CH:9]1[CH2:8][CH2:7][N:6]([CH:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:35](=[O:36])[C:34]2[C:38]([CH3:42])=[CH:39][CH:40]=[CH:41][C:33]=2[CH3:32])[CH2:11][CH2:10]1Participants
Procedure
Using general procedure E, [1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(5-chloro-2-fluoro-benzyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine (see EXAMPLE 215) (86 mg, 0.19 mmol) and 2,6-dimethyl-benzoic acid (40 mg, 0.27 mmol) gave COMPOUND 216 as a white foam (94 mg, 84%). 1H NMR (CDCl3) δ 0.83-1.14 (m, 2H), 0.98 (d, 3H, J=6.6 Hz), 1.47-1.57 (m, 1H), 1.66-1.81 (m, 3H), 2.06-2.17 (m, 1H), 2.30 (s, 6H), 2.46-2.57 (m, 1H), 2.69-2.90 (m, 3H), 3.22-3.33 (m, 1H), 3.36-3.47 (m, 1H), 3.75 (s, 2H), 3.81-3.93 (m, 1H), 4.12-4.23 (m, 4H), 6.07-6.17 (m, 2H), 6.66 (d, 1H, J=8.7 Hz), 6.87-7.04 (m, 4H), 7.10-7.18 (m, 2H), 8.36 (s, 1H). 13C NMR (CDCl3) δ 13.25, 18.99, 28.82, 30.02, 30.90, 39.54, 42.59 (d, J=3.8 Hz), 43.57, 52.01, 57.47, 60.23, 64.04, 64.56, 103.36, 107.81, 116.24 (d, J=23.2 Hz), 117.28, 127.13, 127.77 (d, J=8.1 Hz), 128.32 (d, J=5.5 Hz), 128.35, 129.20 (d, J=3.2 Hz), 129.35 (d, J=15.3 Hz), 133.61, 135.82, 138.27, 143.27, 143.66, 158.57 (d, J=245 Hz), 169.89. ESI-MS m/z 580 (MH)+, 582 (MH+2)+. Anal. Calcd. for C33H39ClFN3O3.0.3H2O.0.2CH2Cl2: C, 66.55; H, 6.72; N, 7.02; Cl, 7.70. Found: C, 66.44; H, 6.60; N, 7.12; Cl, 7.74.
Sources & evidence
- ORD record
- ord-fb6bec81c0814bf9bf6dbcde54227710
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
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