Isopropylamine → N-cyclopropylsulfonyl-13-methyl-2,14-dioxo-17-[2-(propan-2-ylamino)pyrimidin-4-yl]oxy-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

HRID 1429159Notes

Reaction equation

[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=4)[CH2:20][CH:19]3[C:31]([N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=C)[CH3:34])=[O:32])=[O:17])[CH2:12][CH:11]2[CH:13]=C)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:41]([NH2:44])([CH3:43])[CH3:42]>C1COCC1.ClCCCl>[CH:41]([NH:44][C:26]1[N:25]=[C:24]([O:23][CH:21]2[CH2:22][CH:18]3[CH:19]([C:31](=[O:32])[N:33]([CH3:34])[CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH:13][CH:11]4[C:10]([C:8]([NH:7][S:4]([CH:1]5[CH2:3][CH2:2]5)(=[O:6])=[O:5])=[O:9])([NH:15][C:16]3=[O:17])[CH2:12]4)[CH2:20]2)[CH:29]=[CH:28][N:27]=1)([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 150 °C

Procedure

Compound 10f (30 mg, 0.05 mmol) and isopropylamine (excess) in THF (10 ml) was heated in a microwave oven at 110° C. for 30 min and then left at ambient temperature for 16 hrs. The solvent was stripped of and the residue was redissolved in DCE (15 ml) and degassed with nitrogen. Hoyeda-Grubbs II catalyst (7 mg) was added and the mixture was heated in a microwave oven at 150° C. for 10 min. The mixture was concentrated to dryness and purified by prep. HPLC-MS-UV which gave the pure title compound (3.1 mg), (M+H)+=589.2.

Workup

customdegassed with nitrogen
additionHoyeda-Grubbs II catalyst (7 mg) was added
concentrationThe mixture was concentrated to dryness
custompurified by prep

Sources & evidence

ORD record: ord-4de7c34782bd476aa8aed69a69286c35
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937080B2

Reaction notes

Loading…