Diisopropanolamine → HCID 86637940, compound

HRID 1865806Notes

Reaction equation

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

Participants

Reactant 2

HCID 8086Diisopropanolamine

HCID 24755819HCID 24755819, compound

Product 1

HCID 86637940HCID 86637940, compoundYield 100.5%

Procedure

Reaction of 2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (17) (1.02 g) [For method of preparation see co-pending NZ Application No. 521851] with diisopropanolamine (0.8 g) as above gave 2-[bis(2-hydroxypropanyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (18) (1.29 g, 100%): as a yellow foam; 1H NMR [(CD3)2SO] δ 9.22 (br, 1 H), 8.66 (d, J=2.8 Hz, 1 H), 8.29 (d, J=2.8 Hz, 1 H), 4.99 (m, 1 H), 4.85 (br, 1 H), 4.62 (br, 1 H), 3.94 (m, 2 H), 3.77 (m, 2 H), 3.53 (m, 4 H), 3.26 (m, 2 H), 1.48 (m, 10 H), 0.98 (m, 6 H); 13C NMR δ 166.5, 147.8, 142.4, 138.2, 132.6, 128.8, 123.8, 98.1, 64.8, 63.5, 61.5, 60.1, 30.1, 25.0, 20.5, 20.2, 19.1. HRMS (FAB) Calcd. For C20H31N4O9 [M+H+] m/z 471.2091. Found; 471.2089.

Sources & evidence

ORD record: ord-3dbc9c86cc794d06a09c5951496b3ec1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629332B2

Reaction notes

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