2-Iodo-5-methoxy-1,3-benzothiazole → 3-(5-Methoxybenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1926413Notes

Reaction equation

HRID 1926413 reaction equation
F[C:2]1[C:10]2[S:9][C:8]([C:11]3[C:12]([NH2:28])=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)[CH:21]=4)[CH:16]=3)=[N:7][C:6]=2[C:5](C(F)(F)F)=[CH:4][CH:3]=1.IC1SC2C=C[C:40]([O:43]C)=CC=2N=1>>[CH3:40][O:43][C:4]1[CH:3]=[CH:2][C:10]2[S:9][C:8]([C:11]3[C:12]([NH2:28])=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)[CH:21]=4)[CH:16]=3)=[N:7][C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 189669722-Iodo-5-methoxy-1,3-benzothiazoleHCID 67520656HCID 67520656, compound

Product 1

HCID 675209663-(5-Methoxybenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Procedure

Following the procedure for 3-(7-fluoro-4-trifluoromethylbenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine, using 2-iodo-5-methoxy-1,3-benzothiazole and conducting the Suzuki coupling at 55° C. for 4 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=8.75 (s, 1H), 8.40 (s, 1H), 8.34 (s, 1H), 8.06 (s, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.69 (d, J=2.4 Hz, 1H), 7.21 (dd, J=2.4, 8.8 Hz, 1H), 4.67 (m, 1H), 3.94 (s, 3H), 3.59-3.62 (m, 2H), 3.25-3.27 (m, 2H), 2.34-2.39 (m, 4H). MS(ES+): m/z=407.13 [MH+]. HPLC: tR=1.12 min (polar—5 min, ZQ3).

Workup

  1. customat 55° C.
  2. customfor 4 h

Sources & evidence

ORD record
ord-520b7c704407440dac36aab304225b67
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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