Diisopropylethylamine → HCID 69410556, compound

HRID 1592781Notes

Reaction equation

HRID 1592781 reaction equation
FC(F)(F)C(C(O)=O)=O.[NH2:10][CH:11]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][N:27]2[CH:31]=[N:30][CH:29]=[N:28]2)[CH2:16][CH2:15]1)=[O:13].[CH:40]([N:43]1[CH2:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]1[CH2:52][C:53](O)=[O:54])([CH3:42])[CH3:41].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][CH:11]([NH:10][C:53](=[O:54])[CH2:52][C@@H:44]2[C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:51][N:43]2[CH:40]([CH3:41])[CH3:42])[C:12](=[O:13])[N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)[CH2:16][CH2:15]2)=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17952314HCID 17952314, compoundHCID 86592261HCID 86592261, compound

Product 1

HCID 69410556HCID 69410556, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-3-(4-chloro-phenyl)-1-[4-(2-[1,2,4]triazol-1-ylmethyl-phenyl)-piperazin-1-yl]-propan-1-one trifluoroacetyl carboxylate salt(0.30 g, 0.55 mmol), (2-isopropyl-2,3-dihydro-1H-isoindol-1-yl)-acetic acid (0.12 g, 0.55 mmol), HATU (0.21 g, 0.55 mmol) in DCM was added DIPEA (0.19 mL, 1.13 mmol). After about 3 hours, the solution was purified by silica gel chromatography (eluent: 3% 2.0M NH3 in MeOH/DCM). The purified fractions were combined and concentrated under reduced pressure to give the final compound as white foam (0.06 g, 18%). ES MS 626.3 (M+H)

Workup

  1. customthe solution was purified by silica gel chromatography (eluent: 3% 2.0M NH3 in MeOH/DCM)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1125de71882f490892ffaa17440ce428
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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