Isopropylamine → HCID 57496316, compound

HRID 719482Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=4[F:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH:31]([NH2:34])([CH3:33])[CH3:32].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26]([NH:34][CH:31]([CH3:33])[CH3:32])=[CH:25][C:24]=4[F:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-[1-(2-fluoro-4-iodo-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (263 mg, 0.50 mmol), isopropylamine (450 μL, 5.0 mmol), L-proline (86 mg, 0.75 mmol), copper iodide (95 mg, 0.50 mmol) and potassium carbonate (207 mg, 1.50 mmol) in DMSO (4.0 mL) was heated under microwave irradiation for 50 min at 100° C. The crude mixture was concentrated in vacuo and purified by HPLC to provide Compound A230 as a white solid (80 mg, 35%). 1H NMR (CDCl3, 400 MHz) δ 1.20 (d, 6H), 1.26 (d, 6H), 1.75–1.88 (m, 2H), 1.98–2.09 (m, 2H), 3.28–3.37 (m, 2H), 3.55–3.63 (m, 1H), 3.78–3.87 (m, 2H), 4.88 (h, 1H), 5.55 (h, 1H), 6.90–7.08 (m, 2H), 7.44–7.50 (m, 1H), 8.17 (s, 1H), 8.53 (s, 1H). Exact mass calculated for C23H29FN6O3 456.51, found 457.3 (MH+).

Workup

concentrationThe crude mixture was concentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-3ba4b9837aa14611856d9fc3e831b8fc
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132426B2

Reaction notes

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