tert-butyl (2S)-2-[5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate → [2-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidin-1-yl}-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl ester

HRID 1751491Notes

Reaction equation

HRID 1751491 reaction equation
[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Br:31])[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[C:33]([O:37][C:38](N1CCCC1C1NC(C2C=CC3C(=CC=C(Br)C=3)C=2)=CN=1)=O)(C)(C)C.COC(NC(C1CCOCC1)C(O)=O)=O>>[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([CH:6]1[CH2:8][CH2:38][O:37][CH2:33][CH2:7]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Br:31])[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10]

Participants

4

Reactant 3

HCID 58185449tert-butyl (2S)-2-[5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylateHCID 585162412-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 66620357(1-{2-[5-(6-Bromonaphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Product 1

HCID 69675007[2-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidin-1-yl}-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl esterYield 43%

Procedure

This compound was synthesized using the same procedure used to synthesize (1-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester from 2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.469 g, 1.13 mmol) using Methoxycarbonylamino-(tetrahydro-pyran-4-yl)-acetic acid (0.295 g, 1.356 mmol). [2-{2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidin-1-yl}-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl ester (0.264 g, 43% yield). LCMS-ESI+: calc'd for C26H29BrN4O4: 540.14 (M+); Found: 542.08 (M+H+).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-101f0b155fab4366b399e4f28a851b3f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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