4-(Trifluoromethoxy)phenylboronic acid → HCID 71227156, compound

HRID 2409934Notes

Reaction equation

HRID 2409934 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH:23][C:24]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32](OC(F)(F)F)[CH:31]=4)[CH:27]=[CH:26][N:25]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:41][C:42]([F:54])([F:53])[O:43]C1C=CC(B(O)O)=CC=1>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH:23][C:24]3[CH:29]=[C:28]([C:30]4[CH:31]=[CH:32][C:33]([O:43][C:42]([F:54])([F:53])[F:41])=[CH:34][CH:35]=4)[CH:27]=[CH:26][N:25]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 71227252HCID 71227252, compound

Product 1

HCID 71227156HCID 71227156, compound

Procedure

(1R,2R)—N1-((S)-1-(4-Nitrophenyl)piperidin-3-yl)-N2-(4-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)cyclohexane-1,2-diamine (1.4 mg, 0.003 mmol, 6.0% yield) was synthesized as described in General Procedure I using Intermediate A from Example 23 (20 mg, 0.04 mmol) and 4-(trifluoromethoxy)phenylboronic acid (12.2 mg, 0.04 mmol). The desired fraction from RP prep-HPLC method D was concentrated to give the title compound as a pale yellow solid. Anal. Calcd. for C29H32F3N5O3 m/z 555.2, found: 556.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 8.11 (d, J=5.6 Hz, 1H), 8.01 (d, J=9.2 Hz, 2H), 7.57 (d, J=4.4 Hz, 2H), 7.30 (d, J=8 Hz, 2H), 6.78 (d, J=5.6 Hz, 1H), 6.66 (d, J=9.3 Hz, 2H), 6.51 (s, 1H), 4.7 (bs, 1H), 3.72 (m, 1H), 3.62 (m, 2H), 3.54 (m, 1H), 3.05 (m, 1H), 2.9 (m, 2H), 2.53 (m, 1H), 2.14 (m, 3H), 1.96 (m, 1H), 1.78 (m, 4H), 1.27 (m, 6H).

Workup

  1. custom(1R,2R)—N1-((S)-1-(4-Nitrophenyl)piperidin-3-yl)-N2-(4-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)cyclohexane-1,2-diamine (1.4 mg, 0.003 mmol, 6.0% yield) was synthesized
  2. concentrationThe desired fraction from RP prep-HPLC method D was concentrated

Sources & evidence

ORD record
ord-57a10252541249a38f1acbbce9e5eea5
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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