2-Chloro-5-(trifluoromethyl)-1,3-benzothiazole → 5-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(5-trifluoromethylbenzothiazol-2-yl)-pyridin-2-ylamine

HRID 1926391Notes

Reaction equation

HRID 1926391 reaction equation
F[C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH:19]=4)[CH:14]=3)[S:8][C:4]=2[CH:3]=1.ClC1SC2C=CC([C:39]([F:42])([F:41])[F:40])=CC=2N=1>>[NH:23]1[CH2:22][CH2:21][CH:20]([N:18]2[CH:19]=[C:15]([C:13]3[CH:14]=[C:9]([C:7]4[S:8][C:4]5[CH:3]=[CH:2][C:28]([C:39]([F:42])([F:41])[F:40])=[CH:27][C:5]=5[N:6]=4)[C:10]([NH2:26])=[N:11][CH:12]=3)[CH:16]=[N:17]2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 219858492-Chloro-5-(trifluoromethyl)-1,3-benzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 675216505-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(5-trifluoromethylbenzothiazol-2-yl)-pyridin-2-ylamine

Procedure

Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 2-chloro-5-trifluoromethyl-1,3-benzothiazole in place of 2-chloro-6-fluorobenzothiazole to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.12-2.30 (m, 4H), 3.04-3.17 (m, 2H), 3.36-3.45 (m, 2H), 4.48-4.58 (m, 1H), 7.84 (dd, J=8.6, 1.2 Hz, 1H), 8.07 (s, 1H), 8.40-8.44 (m, 2H), 8.46 (d, J=8.4 Hz, 1H), 8.54 (s, 1H), 8.57 (d, J=2.2 Hz, 1H). MS (ES+): m/z=445.09 [MH+]. HPLC: tR=2.39 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-bfa3f590ac01491abf12111fe8cd9598
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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