Diisopropylethylamine → HCID 11487307, compound

HRID 2375787Notes

Reaction equation

HRID 2375787 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][CH:15]=[C:14]3[C:18]([OH:20])=O)[CH:8]=2)=[CH:4][CH:3]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.Cl.Cl.[CH:54]([N:57]1[CH2:62][CH2:61][CH:60]([NH2:63])[CH2:59][CH2:58]1)([CH3:56])[CH3:55]>C(Cl)Cl.COCCOC>[CH:54]([N:57]1[CH2:62][CH2:61][CH:60]([NH:63][C:18]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[CH:17]=[CH:16][CH:15]=2)=[O:20])[CH2:59][CH2:58]1)([CH3:56])[CH3:55]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 69289214HCID 69289214, compound

Product 1

HCID 11487307HCID 11487307, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrole-2-carboxylic acid (62 mg) in DCM (5 mL) was added HOAt (27 mg), EDCI hydrochloride (38 mg) and DIEA (106 μL). The mixture was stirred for 30 min at RT. 1-Isopropyl-piperidin-4-ylamine dihydrochloride (47 mg) and DME (1 mL) were added and stirring was continued for 16 h at RT. The mixture was concentrated in vacuo and the residue was purified by preparative HPLC. The fractions containing the product were evaporated to provide 66 mg of 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide as its trifluoroacetate salt, MS (ESI+): m/e 433 [M+H]+, chloro pattern.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h at RT
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC
  5. additionThe fractions containing the product
  6. customwere evaporated

Sources & evidence

ORD record
ord-c933c61a712e4d74bd44888261b4e4e6
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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