2-(1-methyl-1H-indol-3-yl)acetic acid → N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide

HRID 2369980Notes

Reaction equation

HRID 2369980 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[CH2:10]1.[CH3:23][N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][C:34](O)=[O:35])=[CH:25]1>>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C@@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]3[NH:1][C:34](=[O:35])[CH2:33][C:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]([CH3:23])[CH:25]=3)[CH2:10]2)=[CH:16][CH:17]=1)#[N:20]

Participants

3

Reactant 2

HCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 712264274-(3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile

Product 1

HCID 71226691N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamideYield 32%

Procedure

N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide (15 mg, 0.031 mmol) was synthesized in 32% yield using the procedures described in General Procedure I using 4-(3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (30 mg, 0.10 mmol) and 2-(1-methyl-1H-indol-3-yl)acetic acid (19.02 mg, 0.10 mmol). Anal. Calcd. for C29H35N5O m/z 469.6, found: 470.3 (M+H)+; 1H NMR (500 MHz, MeOH-d3) δ ppm 7.61-7.47 (m, 3H), 7.23 (d, J=8.25 Hz, 1H), 7.14 (t, J=7.70 Hz, 1H), 7.07-6.97 (m, 2H), 6.89 (d, J=8.80 Hz, 2H), 3.80 (dd, J=11.00, 6.60 Hz, 1H), 3.58 (s, 3H), 3.48 (s, 2H), 3.28-3.11 (m, 4H), 3.00-2.91 (m, 1H), 2.87 (dd, J=13.20, 7.15 Hz, 1H), 2.19 (d, J=13.75 Hz, 1H), 2.05-1.92 (m, 2H), 1.90-1.71 (m, 3H), 1.67-1.49 (m, 4H), 1.44-1.34 (m, 2H).

Sources & evidence

ORD record
ord-4833aab5d7194f5baeaaede837b82f12
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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