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Diisopropylethylamine → HCID 10323906, compound

HRID 900246
Notes
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Reaction equation

HRID 900246 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[C:9]([C:23]([OH:25])=O)=[CH:8][N:7]=1)=[O:5].ON1C2N=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C.[CH:57]([N:60]1[CH2:65][CH2:64][CH:63]([NH2:66])[CH2:62][CH2:61]1)([CH3:59])[CH3:58]>CN(C=O)C.C(Cl)Cl>[CH2:2]([O:3][C:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[C:9]([C:23](=[O:25])[NH:66][CH:63]2[CH2:64][CH2:65][N:60]([CH:57]([CH3:59])[CH3:58])[CH2:61][CH2:62]2)=[CH:8][N:7]=1)=[O:5])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31633331-(Propan-2-yl)piperidin-4-amineHCID 69112541HCID 69112541, compound

Product 1

HCID 10323906
HCID 10323906, compound
Yield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 12 mg of 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-2,4-dicarboxylic acid 2-ethyl ester (ii) in DMF (0.5 mL) and DCM (0.5 mL) was added successively 1-Hydroxy-7-azabenzotriazole (5 mg), N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (7 mg) and diisopropyl ethylamine (26 μL). The mixture was stirred for 15 min at RT. 7 mg of 1-Isopropyl-piperidin-4-ylamine (dihydrochloride) were added and stirring was continued at RT. After 2 h the mixture was concentrated in vacuo and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated to provide 8.5 mg of the title compound as its trifluoroacetate salt. Yield: 8.5 mg; MS (ESI+): m/e=505, chloro pattern.

Workup

  1. stirringstirring
  2. customwas continued at RT
  3. concentrationAfter 2 h the mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC (
  5. washC18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA)
  6. additionThe fractions containing the product
  7. customwere evaporated

Sources & evidence

ORD record
ord-ab18eeb1179c42bc8200c4f100360ff3
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07358268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes