Diisopropylethylamine → HCID 11421420, compound

HRID 2375802Notes

Reaction equation

HRID 2375802 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]=[C:16](C(=O)NC4CCN(C(C)C)CC4)[CH:15]=[C:14]3[C:30]([OH:32])=O)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:33][N:34]([C:36]([O:40]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:57][CH2:58][N:59]([CH:63]([CH3:65])[CH3:64])[CH:60]([CH3:62])C.[CH3:66][O:67][CH:68]1[CH2:71][NH:70][CH2:69]1>C(Cl)Cl>[CH:63]([N:59]1[CH2:58][CH2:57][CH:33]([NH:34][C:36]([C:17]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)[C:14]([C:30]([N:70]3[CH2:71][CH:68]([O:67][CH3:66])[CH2:69]3)=[O:32])=[CH:15][CH:16]=2)=[O:40])[CH2:62][CH2:60]1)([CH3:64])[CH3:65]

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 11179038HCID 11179038, compoundHCID 134019963-Methoxyazetidine

Product 1

HCID 11421420HCID 11421420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid (example 17, 9 mg) in DCM (2 mL) was added HATU (7.2 mg), DIEA (13 μL) and 3-methoxy-azetidine. The mixture was stirred for 1 h at RT and then concentrated. The residue was purified by preparative HPLC(CH3CN/H2O gradient+0.05% TFA) to give 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(3-methoxy-azetidine-1-carbonyl)-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (4.3 mg) as its trifluoroacetate salt. MS (ESI+): m/e=546 [M+H]+, chloro pattern.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC(CH3CN/H2O gradient+0.05% TFA)

Sources & evidence

ORD record
ord-eda384904ddb4c5e866586325d01b818
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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