N-bromobutanimide → tert-butyl N-[(10R,14S)-4-bromo-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate

HRID 1481306Notes

Reaction equation

HRID 1481306 reaction equation
[CH3:1][C@@H:2]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]2[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:29].C1C(=O)N([Br:37])C(=O)C1>C(#N)C>[Br:37][C:8]1[CH:7]=[CH:6][C:5]2[NH:4][C:3](=[O:29])[C@H:2]([CH3:1])[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:15]3[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=3)[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 131736623tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate

Product 1

HCID 118236054tert-butyl N-[(10R,14S)-4-bromo-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 45G (616 mg, 1.558 mmol) in acetonitrile (15.200 ml) in a sealed vial was added NBS (277 mg, 1.558 mmol). The reaction was sealed and heated at 75° C. overnight. Additional NBS (300 mg, 1.686 mmol) was added and heat at 75° C. overnight. The mixture was concentrated and purified by silica gel chromatography to afford 137A as a white solid (664 mg, 90%). MS (ESI) m/z: 476.0 (M+H)+.

Workup

  1. customThe reaction was sealed
  2. temperatureheat at 75° C. overnight
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2879cb476296427eb8ba6f435a98ae6e
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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