1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67442505, compound

HRID 1667265Notes

Reaction equation

HRID 1667265 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.Br.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[CH2:33][NH:32][CH2:31]2.C(N=C=NCCCN(C)C)C>ClCCl>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](=[O:15])[N:32]3[CH2:31][C:30]4[C:34](=[CH:35][CH:36]=[C:28]([C:27]([F:26])([F:38])[F:37])[CH:29]=4)[CH2:33]3)[C:9]2=[O:17])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acidHCID 673590385-(Trifluoromethyl)isoindoline hydrobromide

Product 1

HCID 67442505HCID 67442505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.200 g, 0.604 mmol; Example 58D) and 5-(trifluoromethyl)isoindoline hydrobromide (0.178 g, 0.664 mmol) in dichloromethane (0.5 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (0.160 mL, 0.905 mmol) and the reaction stirred for 3 days. The reaction was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=20 mL/minute) over 30 minutes to give the title compound. MS (ESI+) m/z 501.1 (M+H)+.

Workup

  1. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=20 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-d151ad237df5456a9097b87ab9621d69
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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