Carbonochloridic acid, (4-methoxyphenyl)methyl ester → HCID 86690222, compound

HRID 2370004Notes

Reaction equation

HRID 2370004 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23](=[O:35])CC3C4C(=CC=CC=4)N(C)C=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)[O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23](=[O:35])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 13305526Carbonochloridic acid, (4-methoxyphenyl)methyl esterHCID 71226691HCID 71226691, compound2×

Product 1

HCID 86690222HCID 86690222, compound

Procedure

4-Methoxybenzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (41 mg, 0.14 mmol) and 4-methoxybenzyl carbonochloridate (45.8 mg, 0.15 mmol) according to General Procedure H to give 28 mg (44%) of light brown solid. Anal. Calcd. for C27H34N4O3 m/z 462.3, found: 463.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.2 Hz, 2H), 7.04 (d, J=8.77 Hz, 1H), 6.96 (d, J=8.9 Hz, 2H), 6.87 (d, J=8.2 Hz, 2H), 4.94 (m, 2H), 3.86 (m, 1H), 3.73 (s, 4H), 3.08 (m, 1H), 2.76 (m, 1H), 2.36 (m, 2H), 1.90 (m, 1H), 1.80 (m, 2H), 1.65 (m, 1H), 1.45 (m, 1H), 1.18 (m, 5H), 1.02 (m, 1H).

Workup

  1. customto give 28 mg (44%) of light brown solid

Sources & evidence

ORD record
ord-a7feaeda688f4c66aeb19ddaef5412b4
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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