HCID 67520656, compound → 3-(5-Methylbenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1926415Notes

Reaction equation

HRID 1926415 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.I[C:34]1SC2C=CC(C)=CC=2N=1>>[CH3:34][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 67520656HCID 67520656, compoundHCID 675211012-Iodo-5-methylbenzo[d]thiazole

Product 1

HCID 675212673-(5-Methylbenzothiazol-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-methyl-1,3-benzothiazole and conducting the Suzuki coupling at 80° C. for 3 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=8.96-8.87 (brm, 1H), 8.75-8.65 (brm, 1H), 8.51 (d, J=2.0 Hz, 1H), 8.40 (s, 1H), 8.37 (brs, 1H), 8.35 (very brs, 1H), 8.06 (d, J=8.0 Hz, 1H), 8.06 (s, 1H), 7.36 (dd, J=8.0, 1.0 Hz, 1H), 4.56-4.48 (mc, 1H), 3.11 (brq, J=11.0 Hz, 2H), 2.30-2.10 (m, 4H); CH3 and additional 2H hidden under water peak. MS(ES+): m/z=391.14 (72) [MH+], 308.09 (100) [MH+-piperidine]. HPLC: tR=2.10 min (polar—5 min, ZQ2).

Workup

  1. customat 80° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-fd885ad1a2124274b7046f49ecf95292
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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