HCID 73738617, compound → HCID 54704639, compound

HRID 2214734Notes

Reaction equation

HRID 2214734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C:7](=[O:17])[CH:8]=[C:9]1[C:13](=[O:14])OC(C)(C)[O:10]1.[CH2:32]=O.[NH2:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C:7]([C:8]1[CH2:32][N:34]([CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[C:13](=[O:14])[C:9]=1[OH:10])=[O:17]

Participants

4

Reactant 2

HCID 73738617HCID 73738617, compoundHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 54704639HCID 54704639, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(3-morpholin-4-yl-propoxy)-acetamide (0.200 g, 0.42 mmol) with the paraformaldehyde-N-(2-aminoethyl)morpholine adduct in methanol using a procedure similar to the one described in the preparation of compound 13 gave 0.160 g (68% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 1.56 (2H, m, CH2), 2.18 (2H, t, J=7.1 Hz, NCH2), 2.25 (4H, broad, 2×NCH2), 2.39 (4H, broad, 2×NCH2), 2.46 (2H, t, J=6.1 Hz, CH2), 3.50 (2H, t, J=6.1 Hz, NCH2), 3.54 (8H, broad, 4×OCH2), 3.71 (2H, broad t, OCH2), 3.99 (2H, s, NCH2), 4.87 (2H, s, NCH2), 7.40 (1H, broad d, aromatic), 7.58 (1H, d, J=8.1 Hz, aromatic), 7.73 (1H, broad s, aromatic). HRMS (FAB+) calculated for C25H35Cl2N4O6: [M+H]+: 557.193366. found: 557.192134.

Sources & evidence

ORD record
ord-267f42ace52949fca2ff394c015d1022
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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