Triethylamine → HCID 21897690, compound

HRID 1958401Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([S:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[C:16]2[CH:15]=[N:14]1.Cl[C:30]1[N:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][N:31]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:36]([C:33]1[CH:32]=[N:31][C:30]([N:26]2[CH2:25][CH2:24][CH:23]([S:22][C:21]3[N:20]=[CH:19][N:18]=[C:17]4[N:13]([C:4]5[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:8][C:3]=5[F:2])[N:14]=[CH:15][C:16]=34)[CH2:28][CH2:27]2)=[N:35][CH:34]=1)[CH3:37]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (250 mg, 0.56 mmol), 2-chloro-5-ethyl-pyrimidine (680 μL, 5.6 mmol), and triethylamine (315 μL, 2.24 mmol) in isopropanol (4 mL) was heated under microwave irradiation for 15 min at 150° C. The crude mixture was concentrated in vacuo and purified by HPLC to provide Compound A237 as a white solid (100 mg, 35%). 1H NMR (CDCl3, 400 MHz) δ 1.18 (t, 3H), 1.82-1.94 (m, 2H), 2.28-2.37 (m, 2H), 2.53 (q, 2H), 3.06 (s, 3H), 3.55-3.64 (m, 2H), 4.41-4.55 (m, 3H), 7.82 (m, 3H), 8.24 (s, 1H), 8.37 (s, 2H), 8.74 (s, 1H). Exact mass calculated for C23H24FN7O2S2 513.61, found 514.4 (MH+).

Workup

concentrationThe crude mixture was concentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-f7f45d6c8ce443f096380621c274b707
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410119B2

Reaction notes

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