4-Methylmorpholine → HCID 56961778, compound

HRID 1958102Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:20])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.[C:21](O)(=[O:26])[CH2:22][CH2:23][CH2:24][CH3:25].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([NH:20][C:21](=[O:26])[CH2:22][CH2:23][CH2:24][CH3:25])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (50 mg, 0.165 mmol) and valeric acid (36 mg, 0.247 mmol) in DMF (5 ml) were added N-methyl morpholine (51 mg, 0.5 mmol) and HBTU (94 mg, 0.247 mmol), and the reaction mixture was stirred for 16 h at 25° C. The reaction mixture was poured into water and extracted with ethyl acetate (3×20 ml). The combined ethyl acetate part was dried over Na2SO4 and evaporated to furnish the crude material (60 mg). The crude was purified by prep. HPLC and the desired product (30 mg, 47%) was obtained as sticky white solid. MS (LC/MS): 387.2 (M+H).

Workup

extractionextracted with ethyl acetate (3×20 ml)
dry with materialThe combined ethyl acetate part was dried over Na2SO4
customevaporated
customto furnish the crude material (60 mg)
customThe crude was purified by prep

Sources & evidence

ORD record: ord-b480627750ed42ac9237fbb88c870576
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410107B2

Reaction notes

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