Morpholine → HCID 22594080, compound

HRID 1760978Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:26]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:23])=[C:12]([CH:22]=1)[NH:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](SC)[N:15]=1)=[O:6].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:26]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:23])=[C:12]([CH:22]=1)[NH:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:15]=1)=[O:6]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-[5-(3-fluoro-5-morpholinobenzamido)-2-methylanilino]2-methylthiopyrimidine (0.228 g) and morpholine (1 ml) was stirred and heated to 150° C. for 10 days. The reaction mixture was allowed to cool to ambient temperature and poured into water (10 ml). The resultant precipitate was collected by filtration and dried in a vacuum oven at 60° C. for 16 hours. There was thus obtained the title compound (0.175 g); NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 3.21 (m, 4H), 3.59 (m, 8H), 3.74 (m, 4H), 5.98 (d, 1H), 6.96 (m, 1H), 7.09 (m, 1H), 7.18 (m, 1H), 7.26 (m, 1H), 7.38 (m, 1H), 7.89 (d, 1H), 8.01 (m, 1H), 8.49 (s, 1H), 10.07 (s, 1H); Mass Spectrum: M+H+ 493.

Workup

temperatureto cool to ambient temperature
filtrationThe resultant precipitate was collected by filtration
customdried in a vacuum oven at 60° C. for 16 hours

Sources & evidence

ORD record: ord-24ea405295ba4d839ca8349d49cbc8e0
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846827B1

Reaction notes

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