3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 71227252, compound

HRID 2409933Notes

Reaction equation

HRID 2409933 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[CH2:17]2)[CH:3]=1.[F:31][C:32]([F:44])([F:43])[O:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1>>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([N:18]2[CH2:19][CH2:20][CH2:21][C@H:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]3[NH:8][C:4]3[CH:3]=[C:2]([C:36]4[CH:37]=[CH:38][CH:39]=[C:34]([O:33][C:32]([F:31])([F:43])[F:44])[CH:35]=4)[CH:7]=[CH:6][N:5]=3)[CH2:17]2)=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

3

Reactant 2

HCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 71233298HCID 71233298, compound

Product 1

HCID 71227252HCID 71227252, compound

Procedure

(1R,2R)—N1-((S)-1-(4-Nitrophenyl)piperidin-3-yl)-N2-(4-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)cyclohexane-1,2-diamine (1.6 mg, 0.003 mmol, 6.8% yield) was synthesized as described in General Procedure I using (1R,2R)—N1-(4-bromopyridin-2-yl)-N2-((S)-1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (20 mg, 0.04 mmol) and 3-(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 8.05 (d, J=2.0 Hz, 1H), 7.80 (m, 2H), 7.51 (m, 1H), 7.39 (m, 1H), 7.33 (m, 2H), 6.89 (dd, J=5.6 Hz, J=1.6 Hz, 1H), 6.77 (m, 2H), 6.47 (m, 1H), 4.09 (m, 1H), 3.70 (m, 3H), 3.23 (m, 1H), 3.11 (m, 1H), 2.92 (m, 1H), 2.36 (m, 1H), 2.11 (m, 3H), 1.92 (m, 4H), 1.64 (m, 2H), 1.44 (m, 2H).

Workup

  1. custom(1R,2R)—N1-((S)-1-(4-Nitrophenyl)piperidin-3-yl)-N2-(4-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)cyclohexane-1,2-diamine (1.6 mg, 0.003 mmol, 6.8% yield) was synthesized
  2. concentrationThe desired fraction from RP prep-HPLC method D was concentrated

Sources & evidence

ORD record
ord-b9417ae55da74797817adf08452f14a9
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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