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

HRID 1424939Notes

Reaction equation

HRID 1424939 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].[CH3:17][C:18]1[NH:22][C:21]([C:23](O)=[O:24])=[N:20][C:19]=1[C:26]([F:29])([F:28])[F:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>>[CH3:17][C:18]1[NH:22][C:21]([C:23]([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:24])=[N:20][C:19]=1[C:26]([F:29])([F:27])[F:28]

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 675498085-methyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid

Product 1

HCID 86648482tert-Butyl cis(+/-)-4-{[(5-methyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

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) (0.22 g, 0.96 mmol), 5-methyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid obtained in Example (36d) (0.10 g, 0.51 mmol), WSC hydrochloride (0.30 g, 1.57 mmol) and HOBT (70 mg, 0.52 mmol), to obtain 0.17 g of the title compound as a white foamy substance (83%).

Workup

  1. customobtained by the method

Sources & evidence

ORD record
ord-ae2eda905d2746518509723dac6ef43e
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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