1-Hydroxybenzotriazole → tert-Butyl cis(+/-)-4-{[(5-ethyl-4-iodo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

HRID 1424977Notes

Reaction equation

HRID 1424977 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH3:16].[CH2:17]([C:19]1[NH:23][C:22]([C:24](O)=[O:25])=[N:21][C:20]=1[I:27])[CH3:18].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH2:17]([C:19]1[NH:23][C:22]([C:24]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]2[O:15][CH3:16])=[O:25])=[N:21][C:20]=1[I:27])[CH3:18]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine2×HCID 675488385-ethyl-4-iodo-1H-imidazole-2-carboxylic acid

Product 1

HCID 86648514tert-Butyl cis(+/-)-4-{[(5-ethyl-4-iodo-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylateYield 86%

Procedure

The same operation as in Example (1g) was performed using tert-butyl cis(±)-4-amino-3-methoxypiperidine-1-carboxylate obtained by the method described in Example (1e) (130 mg, 0.56 mmol), 5-ethyl-4-iodo-1H-imidazole-2-carboxylic acid obtained in Example (58b) (95 mg, 0.36 mmol), WSC hydrochloride (220 mg, 1.15 mmol) and HOBT (46 mg, 0.34 mmol), to obtain 146.2 mg of the title compound as a white solid (86%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-4600ac6136bc4dccbdfc890fd3fe2ec9
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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