Dicyclohexylcarbodiimide → HCID 178463452, compound

HRID 921955Notes

Reaction equation

HRID 921955 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH3:17])[C:12]3=[N:18][CH:19]=[C:20]([C:21]#[N:22])[N:11]3[N:10]=2)=[CH:6][C:5]([C:23]#[N:24])=[CH:4][C:3]=1[N:25]1[CH2:30][CH2:29][C@@H:28]([NH:31][C:32](=[O:35])[O:33][CH3:34])[C@H:27]([OH:36])[CH2:26]1.CC(OC([NH:44][C@H:45]([C:67](O)=[O:68])[CH2:46][CH2:47][CH2:48][N:49]=[C:50]([NH:59]C(OC(C)(C)C)=O)[NH:51]C(OC(C)(C)C)=O)=O)(C)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[ClH:1].[ClH:1].[ClH:1].[NH2:44][C@@H:45]([CH2:46][CH2:47][CH2:48][NH:49][C:50]([NH2:59])=[NH:51])[C:67]([O:36][C@H:27]1[C@H:28]([NH:31][C:32]([O:33][CH3:34])=[O:35])[CH2:29][CH2:30][N:25]([C:3]2[CH:4]=[C:5]([C:23]#[N:24])[CH:6]=[C:7]([NH:8][C:9]3[N:14]=[C:13]([NH:15][CH2:16][CH3:17])[C:12]4=[N:18][CH:19]=[C:20]([C:21]#[N:22])[N:11]4[N:10]=3)[C:2]=2[Cl:1])[CH2:26]1)=[O:68]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11385959Boc-arg(boc)2-OHHCID 89932121methyl ((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(ethylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)carbamate

Product 1

HCID 178463452HCID 178463452, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (Example 328) methyl ((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(ethylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)carbamate (50 mg, 0.098 mmol), BOC-ARG(BOC)2-OH (96 mg, 0.202 mmol), DMAP (2.391 mg, 0.020 mmol) and DCC (60.6 mg, 0.294 mmol) were dissolved in DCM (5 mL) under nitrogen. The reaction mixture was stirred at room temperature 12 hr; the LCMS showed complete conversion. The solvent was removed and the material was diluted with acetone and filtered (removes 1,3-dicyclohexylurea).

Workup

  1. customThe solvent was removed
  2. additionthe material was diluted with acetone
  3. filtrationfiltered
  4. custom(removes 1,3-dicyclohexylurea)

Sources & evidence

ORD record
ord-9e9b0693768f44a1955d1165e067d9f7
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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