Imidazole → HCID 86616990, compound

HRID 1944581Notes

Reaction equation

HRID 1944581 reaction equation
[CH2:1]([C@:8]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:37])[C:9]([NH:11][NH:12][C:13](=[O:36])[C:14]1[CH:19]=[C:18]([N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])[N:17]=[C:16]([N:26]([CH2:32][CH2:33][O:34][CH3:35])[CH2:27][CH:28]2[CH2:30][CH:29]2[CH3:31])[CH:15]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.C(Br)(Br)(Br)Br>C(Cl)Cl>[CH3:35][O:34][CH2:33][CH2:32][N:26]([CH2:27][C@@H:28]1[CH2:30][C@H:29]1[CH3:31])[C:16]1[CH:15]=[C:14]([C:13]2[O:36][C:9]([C@@:8]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:42])([CH3:44])[CH3:43])([CH3:37])[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][N:12]=2)[CH:19]=[C:18]([N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])[N:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86616991HCID 86616991, compound

Product 1

HCID 86616990HCID 86616990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1R)-1-benzyl-2-oxo-(2-{2-{(2-methoxyethyl)[(2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]isonicotinoyl}hydrazino)-1-methylethyl]carbamate (16.2 g, 25 mmol), triphenylphosphine (7.88 g, 30.1 mmol) and imidazole (2.05 g, 30.1 mmol) in DCM (150 mL) cooled to 0° C. was added carbon tetrabromide (9.97 g, 30.1 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mixture was concentrated in vacuo, and purified by flash chromatography (silica, 20% to 50% EtOAc in hexane) to give tert-butyl [(1R)-1-(5-{2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]pyridin-4-yl}-1,3,4-oxadiazol-2-yl)-1-methyl-2-phenylethyl]carbamate. MS M+1=629.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 20% to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-9589a7d31f134af9a2993f0fd57ae111
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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