Morpholine → HCID 67064146, compound

HRID 1256300Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

N-(7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D) (1.0 equivalent) and morpholine (2.0 equivalent) were dissolved in dry n-butanol (0.1 M) under nitrogen. The mixture was heated to 100° C. for 18 h. Next day, lower temperature to room temperature, and product precipitates. The precipitate was collected by filtration and then washed with diethyl ether to give the titled compound (54%) as a pink solid. Melting point (225.0-229° C.). 1H NMR (400 MHz, MeOD) δ ppm 3.31 (s, 6 H) 3.70-3.79 (m, 4 H) 3.90-3.98 (m, 4 H) 6.35 (d, J=2.27 Hz, 1 H) 7.40 (s, 1 H) 7.66 (d, J=8.59 Hz, 2 H) 7.94 (d, J=8.59 Hz, 2 H) 8.01 (d, J=2.27 Hz, 1 H). ESI-MS: m/z 382.2 (M+H)+.

Workup

customNext day, lower temperature to room temperature, and product precipitates
filtrationThe precipitate was collected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-105d22a198ec49bda74b64eb3986e126
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461163B2

Reaction notes

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