Water → N-(6-methyl-3,4-dihydro-2H-chromen-4-yl)-N'-quinolin-5-ylurea

HRID 2092158Notes

Reaction equation

N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][CH2:18][CH2:17][CH:16]2[NH2:23].FC(F)(F)C1C=C2C([CH:30]([NH2:36])CCO2)=CC=1.[OH2:39]>>[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][CH2:18][CH2:17][CH:16]2[NH:23][C:30]([NH:36][C:9]1[CH:10]=[CH:11][CH:2]=[C:7]2[C:8]=1[CH:3]=[CH:4][CH:5]=[N:6]2)=[O:39]

Participants

Reactant 4

HCID 962Water

HCID 707665-Aminoisoquinoline

HCID 162444176-Methylchroman-4-amine

HCID 468354217-(Trifluoromethyl)chroman-4-amine

Product 1

HCID 53251494N-(6-methyl-3,4-dihydro-2H-chromen-4-yl)-N'-quinolin-5-ylurea

Procedure

This compound was made following the procedure of Example 5, except substituting 5-aminoquinoline for 5-aminoisoquinoline and 6-methyl-chroman-4-ylamine for 7-trifluoromethyl-chroman-4-ylamine. 1H NMR (300 MHz, DMSO-d6) δ 8.90 (m, 1H), 8.60 (s, 1H), 8.47 (m, 1H), 8.18 (m, 1H), 7.68 (m, 2H), 7.57 (m, 1H), 7.16 (m, 1H), 7.08 (d, J=7.5 Hz, 1H), 7.00 (m, 1H), 6.71 (d, J=7.5 Hz, 1H), 4.93 (m, 1H), 4.31-4.10 (m, 2H), 2.21 (s, 3H), 2.20-1.93 (m, 2H). MS (ESI) m/e 334 (M+H)+. Calcd. For C20H19N3O2.0.1; H2O: C, 71.67; H, 5.77; N, 12.54. Found: C, 71.65; H, 5.83; N, 12.30.

Sources & evidence

ORD record: ord-eb03abf619234e93823692e0bdff27c1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440691B2

Reaction notes

Loading…