Diisopropylethylamine → HCID 22598929, compound

HRID 2252464Notes

Reaction equation

HRID 2252464 reaction equation
[C:1]1([C:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26](O)=[O:27])=[CH:23][CH:24]=3)[CH:19]=[N:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:41][CH2:42][CH:43]([NH:48][S:49]([C:52]1[C:57]([CH3:58])=[CH:56][C:55]([O:59][CH2:60][CH2:61][CH2:62][C:63](=[O:89])[NH:64][CH2:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][CH2:77][NH:78][C:79]([O:81][CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[O:80])=[CH:54][C:53]=1[CH3:90])(=[O:51])=[O:50])[C:44]([O:46][CH3:47])=[O:45].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:58][C:57]1[CH:56]=[C:55]([O:59][CH2:60][CH2:61][CH2:62][C:63](=[O:89])[NH:64][CH2:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][CH2:77][NH:78][C:79]([O:81][CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[O:80])[CH:54]=[C:53]([CH3:90])[C:52]=1[S:49]([NH:48][CH:43]([CH2:42][NH:41][C:26]([C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[N:17]([CH2:16][CH2:15][CH2:14][NH:13][C:9]1[N:8]([C:7]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:12]=[CH:11][N:10]=1)[N:18]=[CH:19]2)=[O:27])[C:44]([O:46][CH3:47])=[O:45])(=[O:51])=[O:50]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10649815HCID 10649815, compoundHCID 21881488HCID 21881488, compound

Product 1

HCID 22598929HCID 22598929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-((1-(triphenylmethyl)imidazol-2-yl)amino)propyl)-1H-indazole-5-carboxylic acid, methyl 3-amino-2-(((2,6-dimethyl-4-(3-(N-(3-(2-(2-(3-((phenylmethoxy)carbonylamino)propoxy)ethoxy)ethoxy)propyl)carbamoyl)propoxy)phenyl)sulfonyl)amino)propanoate, DIEA, and HBTU in anhydrous DMF are stirred at ambient temperatures under nitrogen for 4 h. The DMF is removed under vacuum and the resulting residue is dissolved in EtOAc and washed with water, saturated NaHCO3, and saturated NaCl. The EtOAc layer is dried (MgSO4) and concentrated to dryness. The crude product is purified by flash chromatography on silica gel using EtOAc/MeOH.

Workup

  1. customThe DMF is removed under vacuum
  2. dissolutionthe resulting residue is dissolved in EtOAc
  3. washwashed with water, saturated NaHCO3, and saturated NaCl
  4. dry with materialThe EtOAc layer is dried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-56677de53dcb4dd2892f4ec6774d83ae
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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