Triethylamine → HCID 59856860, compound

HRID 2377910Notes

Reaction equation

[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([C:18](=[O:20])[CH3:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:28]([O:32][C:33](Cl)=[O:34])[CH:29]([CH3:31])[CH3:30].C(N(CC)CC)C>CN(C=O)C>[CH2:28]([O:32][C:33]([N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:16]2[C:17]([C:18](=[O:20])[CH3:19])=[C:12]([NH:11][C:8]3[CH:9]=[N:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=3)[N:13]=[CH:14][N:15]=2)[CH2:23][CH2:24]1)=[O:34])[CH:29]([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[4-(6-methanesulfonyl-pyridin-3-ylamino)-6-(piperidin-4-yloxy)-pyrimidin-5-yl]-ethanone (48 mg, 0.11 mmol), isobutylchloroformate (14.0 μL, 0.11 mmol), and triethylamine (45 μL, 0.34 mmol) in DMF (1.0 mL) was heated under microwave irradiation for 3 minutes at 80° C. The crude mixture was purified by HPLC to provide Compound A60 as a white solid (35 mg, 65%). 1H NMR (CDCl3, 400 MHz) δ 0.97 (d, 6H), 1.82-1.92 (m, 2H), 2.10-2.19 (m, 2H), 2.70 (s, 3H), 3.22 (s, 3H), 3.37 (m, 2H), 3.89-3.96 (m, 5H), 5.59 (h, 1H), 8.10 (d, 1H), 8.49-8.57 (m, 2H), 8.92 (d, 2H). Exact mass calculated for C22H29N5O6S 491.18, found 492.3 (MH+).

Workup

customThe crude mixture was purified by HPLC

Sources & evidence

ORD record: ord-b3cfa26f2b2c44c58fc293d432f401fe
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470699B2

Reaction notes

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