Morpholine → HCID 71765295, compound

HRID 2203242Notes

Reaction equation

HRID 2203242 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:13]3[CH:21]=[C:20]4[C:16]([CH:17]=[N:18][NH:19]4)=[CH:15][C:14]=3[CH3:22])[CH:8]=[C:9](F)[CH:10]=2)[N:5]=[N:4][C:3]=1[C:23]([NH2:25])=[O:24].CCN(C(C)C)C(C)C.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CC(N(C)C)=O>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:13]3[CH:21]=[C:20]4[C:16]([CH:17]=[N:18][NH:19]4)=[CH:15][C:14]=3[CH3:22])[CH:8]=[C:9]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:10]=2)[N:5]=[N:4][C:3]=1[C:23]([NH2:25])=[O:24]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 71765394HCID 71765394, compound

Product 1

HCID 71765295HCID 71765295, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-amino-6-fluoro-8-(5-methyl-1H-indazol-6-yl)cinnoline-3-carboxamide (200 mg, 0.59 mmol), DIPEA (1000 mg), morpholine (500 mg,) and DMA (4 mL) was heated at 140° C. in a microwave under N2 for 3 hours. The mixture was cooled, concentrated, and purified via preparative HPLC to give the title compound (60 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.95 (1H, s), 8.93 (1H, br s), 8.30 (1H, d, J=2.4 Hz), 8.03 (1H, s), 7.81 (1H, br s), 7.60 (1H, s), 7.54-7.51 (3H, m), 7.35 (1H, s), 3.79 (4H, t, J=4.8 Hz), 3.42 (4H, t, J=4.8 Hz), 2.00 (3H, s); LC-MS (5-95% ACN in H2O gradient with 0.02% NH4OAc, tR 3.053 minutes); ESI+APCI m/z [M+H]+ 404.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-9572f9e3a9ab42e5a08e66da3e6bab53
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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