Diisopropylamine → HCID 56953202, compound

HRID 2366237Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:10]3[S:17][C:16]([C:18]4[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:25])=[N:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:3]=1.Cl.N1[CH2:30][CH:29]([OH:31])[CH2:28]1.[CH:32](NC(C)C)(C)C>C(O)C>[Cl:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:25])[C:18]=1[C:16]1[S:17][C:10]2[C:9]([NH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([CH:32]4[CH2:30][CH:29]([OH:31])[CH2:28]4)[CH:3]=3)=[N:14][CH:13]=[N:12][C:11]=2[N:15]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The mixture of N-(6-chloropyrimidin-4-yl)-2-(2,6-dichlorophenyl)-thiazolo[4,5-d]pyrimidin-7-amine (45 mg, 0.11 mmol), azetidin-3-ol hydrochloride (24 mg, 0.22 mmol) and diisopropylamine (45 mg, 0.35 mmol) in ethanol (1 mL) was heated at 130° C. under microwave radiation for 30 minutes. The reaction mixture was concentrated under reduced pressure. The crude product was purified by reverse phase HPLC (Gemini-NX, 3×10 cm, gradient: 5-85% CH3CN/H2O, 0.1% formic acid/H2O, flow rate 60 mL/min, 10 min) to give the desired compound as a white solid (25 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.94 (s, 1H), 8.85 (s, 1H), 8.31 (d, J=0.8 Hz, 1H), 7.78-7.71 (m, 2H), 7.67 (dd, J=9.4, 6.7 Hz, 1H), 6.54 (s, 1H), 5.79 (d, J=6.5 Hz, 1H), 4.69-4.55 (m, 1H), 4.29-4.18 (m, 2H), 3.76 (dd, J=9.4, 4.4 Hz, 2H). LCMS (Method B): RT=3.55 min, m/z: 446.2 [M+H+].

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude product was purified by reverse phase HPLC (Gemini-NX, 3×10 cm, gradient: 5-85% CH3CN/H2O, 0.1% formic acid/H2O, flow rate 60 mL/min, 10 min)

Sources & evidence

ORD record: ord-890d998279e4464a9dda953d545d290c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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