Diisopropylethylamine → HCID 86707975, compound

HRID 75285Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C@@H:17]([NH2:19])[CH3:18])=[C:8]([C:11]3[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=3)[CH:9]=2)[CH:4]=[CH:3]1.[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([F:28])=[CH:23][N:22]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[Cl:20][C:21]1[N:26]=[C:25]([NH:19][C@H:17]([C:7]2[N:6]=[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:10]3=[CH:9][C:8]=2[C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)[CH3:18])[C:24]([F:28])=[CH:23][N:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (90 mg, 0.353 mmol), 2,4-dichloro-5-fluoropyrimidine (88 mg, 0.529 mmol), and N-ethyl-N-isopropylpropan-2-amine (190 μL, 1.058 mmol) were combined in acetonitrile (500 μL). The reaction mixture was heated to 120° C. in a microwave reactor for 1 hour. After removal of solvent, the residue was diluted with MeOH and dichloromethane, and was purified by preparative HPLC, eluting with a gradient of 15-25% ACN in H2O with 0.35% TFA. The fractions were collected and solvent was removed in vacuo to give the title compound (136 mg, 100%). ESI-MS m/z [M+H]+ calc'd for C18H17ClFN7, 386; found 386.

Workup

customAfter removal of solvent
additionthe residue was diluted with MeOH and dichloromethane
customwas purified by preparative HPLC
washeluting with a gradient of 15-25% ACN in H2O with 0.35% TFA
customThe fractions were collected
customsolvent was removed in vacuo

Sources & evidence

ORD record: ord-f36a9811d20043f89336f8f93f0951d7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835420B2

Reaction notes

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