Diisopropylethylamine → HCID 178461870, compound

HRID 415412Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[N:5][C:6]([C@@H:9]([NH2:11])[CH3:10])=[N:7][CH:8]=1.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[NH:22][N:21]=2)[C:16]([Cl:31])=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:31][C:16]1[C:17]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[NH:22][N:21]=2)=[N:18][C:13]([NH:11][C@H:9]([C:6]2[N:7]=[CH:8][C:3]([F:2])=[CH:4][N:5]=2)[CH3:10])=[N:14][CH:15]=1

Participants

Conditions

Temperature: 165 °C

Procedure

To a microwave vial was added (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 81 mg, 0.46 mmol), 2,5-dichloro-N-[5-(2,2,2-trifluoroethoxy)-1H-pyrazol-3-yl]pyrimidin-4-amine (Method 40, 100 mg, 0.31 mmol), and DIEA (110 mg, 0.9 mmol). Anhydrous n-BuOH (2.5 mL) was added, and the vial was heated in microwave oven at 165° C. for 5 hours. The reaction mixture was concentrated. The resulting residue was separated by silica gel column to afford desired product (80 mg, 62%). LC-MS, 433 (M+1). 1H NMR δ 12.19 (s, 1H), 9.76 (s, 1H), 8.83 (s, 2H), 7.92-8.10 (m, 2H), 5.67 (s, 1H), 5.13 (s, 1H), 4.75 (m, 2H), 1.49 (m, 3H).

Workup

concentrationThe reaction mixture was concentrated
customThe resulting residue was separated by silica gel column

Sources & evidence

ORD record: ord-44a9842f25df486e9de12944bfd9da74
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088784B2

Reaction notes

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