3-(4-(Trifluoromethyl)phenyl)propionic Acid → N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)-3-[4-(trifluoromethyl)phenyl]propanamide

HRID 1912963Notes

Reaction equation

HRID 1912963 reaction equation
[C:1]([C:5]1[C:6]([NH2:14])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:29])([F:28])[C:17]1[CH:27]=[CH:26][C:20]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:19][CH:18]=1>>[C:1]([C:5]1[C:6]([NH:14][C:23](=[O:24])[CH2:22][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([C:16]([F:28])([F:29])[F:15])=[CH:27][CH:26]=2)=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 35887363-(4-(Trifluoromethyl)phenyl)propionic AcidHCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68751490N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)-3-[4-(trifluoromethyl)phenyl]propanamide

Procedure

The product from Example 105B and 4-(trifluoromethyl)hydrocinnamic acid were processed using the method analogous to that described in Example 137 to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36 (s, 9H), 2.61-2.73 (m, 2H), 3.00 (t, J=7.5 Hz, 2H), 6.99 (dd, J=7.1, 4.1 Hz, 1H), 7.78-7.51 (m, 2H), 7.63-7.66 (m, 2H), 8.48 (dd, J=4.1, 1.7 Hz, 1H), 8.91 (dd, J=7.1, 1.7 Hz, 1H), 9.75 (s, 1H); MS (DCI) m/z 391 (M+H)+.

Sources & evidence

ORD record
ord-925e73fa611f4630a96620f363cbed2e
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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