1,1'-Carbonyldiimidazole → HCID 57512677, compound

HRID 14227Notes

Reaction equation

HRID 14227 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](O)=[O:15])[CH:12]=2)[C:7]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[CH:6]1)[CH2:2][CH2:3][CH3:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:35][C@@H:36]([CH2:50][C:51]1[CH:56]=[C:55]([F:57])[CH:54]=[C:53]([F:58])[CH:52]=1)[C@H:37]([OH:49])[CH2:38][NH:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][CH3:48])[CH:42]=1>ClCCl>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH:35][C@@H:36]([CH2:50][C:51]3[CH:52]=[C:53]([F:58])[CH:54]=[C:55]([F:57])[CH:56]=3)[C@H:37]([OH:49])[CH2:38][NH:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][CH3:48])[CH:42]=3)=[O:15])[CH:12]=2)[C:7]([C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21085168HCID 21085168, compoundHCID 57487282(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

Product 1

HCID 57512677HCID 57512677, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylic acid (0.141 g) was dissolved in dichloromethane (10 mL). 1,1′-Carbonyldiimidazole (0.080 g) was added and the mixture was stirred at room temperature for 2 h. A solution of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.166 g) in dichloromethane was added and the mixture was allowed to stir overnight at room temperature. The mixture was then partitioned between dichloromethane and water, dried over sodium sulfate, filtered, and concentrated. Chromatography on silica gel using methanol/ethyl acetate/heptane /dichloromethane (3/10/10/77 to 6/10/10/74) gave 1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-3-(trifluoroacetyl)-1H-indole-6-carboxamide (0.155 g). MS (ESI+) for C34H36F5N3O3+H1 m/z 630.28 (M+H)+.

Workup

  1. stirringto stir overnight at room temperature
  2. customThe mixture was then partitioned between dichloromethane and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bca1860bc1bf4cf488fce9029f291919
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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