HCID 67520656, compound → 3-(7-Bromobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1926417Notes

Reaction equation

HRID 1926417 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.[Br:33]C1C2SC(I)=NC=2C=CC=1>>[Br:33][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[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 675212127-Bromo-2-iodobenzo[d]thiazole

Product 1

HCID 441589363-(7-Bromobenzothiazol-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 7-bromo-2-iodo-1,3-benzothiazole and conducting the Suzuki coupling at 60° C. for 4 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=9.20-9.09 (brm, 1H), 9.02-8.90 (brm, 1H), 8.61 (very brs, 1H), 8.60 (s, 2H), 8.52 (s, 1H), 8.18 (d, J=8.0 Hz, 1H), 8.13 (s, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.58 (t, J=8.0 Hz, 1H), 4.57-4.47 (mc, 1H), 3.40 (brd, J=12.8 Hz, 2H), 3.11 (brq, J=11.2 Hz, 2H), 2.31-2.12 (m, 4H). MS(ES+): m/z=454.98/457.00 (79/83) [MH+], 371.94/373.95 (95/100) [MH+-piperidine]. HPLC: tR=2.22 min (polar—5 min, ZQ2).

Workup

  1. customat 60° C.
  2. customfor 4 h

Sources & evidence

ORD record
ord-9ed151b3b08f47d8ae14ad8d06fec58b
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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