Hydrochloric Acid → HCID 178422948, compound

HRID 510408Notes

Reaction equation

O=[C:2]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:26][C:27]1[C:28]([NH2:33])=[N:29][NH:30][C:31]=1[NH2:32].Cl>CO>[NH2:32][C:31]1[C:27]([CH2:26][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([F:24])([F:23])[F:25])[C:16]=2[CH3:15])=[C:28]2[N:33]=[C:2]([CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[CH:3]=[C:4]([OH:6])[N:29]2[N:30]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (0.2 g, 0.999 mmol) and 4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazole-3,5-diamine (0.270 g, 0.999 mmol) was added Methanol (4 mL) and hydrochloric acid (0.4 mL, 0.500 mmol) in methanol (1.25 N). The reaction vessel was sealed and heated at 65° C. for 6 days. The reaction mixture was concentrated to 1 mL. The solid was filtered and wash with methanol (2 ml×3) and dried (0.19 g, 45%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.84 (m, 4H) 2.47 (s, 3H) 2.58-2.75 (m, 1H) 3.34-3.39 (m, 2H) 3.85 (s, 2H) 3.93 (dd, J=11.24, 3.16 Hz, 2H) 5.28 (s, 2H) 5.41 (d, J=1.52 Hz, 1H) 7.01 (d, J=7.83 Hz, 1H) 7.28 (m, 1H) 7.54 (d, J=7.83 Hz, 1H) 11.18 (s, 1H); LC/MS: MS (ES+) m/e 407.2 [M+H]+.

Workup

customThe reaction vessel was sealed
concentrationThe reaction mixture was concentrated to 1 mL
filtrationThe solid was filtered
washwash with methanol (2 ml×3)
customdried (0.19 g, 45%)

Sources & evidence

ORD record: ord-db63da624f9541489142df0c47076f69
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096605B2

Reaction notes

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