Diisopropylethylamine → HCID 24948833, compound

HRID 556454Notes

Reaction equation

HRID 556454 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:34]1([C:40](=[O:42])[CH3:41])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[Cl:43][C:44]1[CH:52]=[C:51]2[C:47]([C:48]([N:62]([CH2:69][C:70](O)=[O:71])[CH:63]3[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]3)([CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[C:57]([Cl:61])[CH:56]=3)[C:49](=[O:53])[NH:50]2)=[CH:46][CH:45]=1>ClCCl>[C:40]([N:34]1[CH2:39][CH2:38][N:37]([C:70](=[O:71])[CH2:69][N:62]([CH:63]2[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]2)[C:48]2([CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[C:57]([Cl:61])[CH:56]=3)[C:47]3[C:51](=[CH:52][C:44]([Cl:43])=[CH:45][CH:46]=3)[NH:50][C:49]2=[O:53])[CH2:36][CH2:35]1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 837951-AcetylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24948832HCID 24948832, compound

Product 1

HCID 24948833HCID 24948833, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of DIPEA (43 mg, 0.33 mmol), HATU (64 mg, 0.17 mmol) and 1-piperazin-1-yl-ethanone (22 mg, 0.17 mmol) in dichloromethane (3 mL) was added rac-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-indol-3-yl]-cyclohexyl-amino}-acetic acid (50 mg, 0.11 mmol). After the mixture was stirred at room temperature for 3 h, the crude was washed with water (3×10 mL). The organic solution was concentrated in vacuo and the residue was puritificated by preparative HPLC to give 24 mg of rac-3-{[2-(4-acetyl-piperazin-1-yl)-2-oxo-ethyl]-cyclohexyl-amino}-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a white solid. MS: 557 (M+H)+.

Workup

  1. washthe crude was washed with water (3×10 mL)
  2. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f8bda49bc6a54ac1a6cc89385336a10b
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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