HCID 67520656, compound → HCID 67520954, compound

HRID 1926438Notes

Reaction equation

HRID 1926438 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:29]([F:32])([F:31])[F:30])=[CH:4][CH:3]=1.[F:33]C1C=CC2SC(I)=NC=2C=1C(F)(F)F>>[F:33][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[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]5)[CH:21]=4)[CH:16]=3)=[N:7][C:6]=2[C:5]=1[C:29]([F:30])([F:31])[F:32]

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 67521813HCID 67521813, compound

Product 1

HCID 67520954HCID 67520954, compound

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 5-fluoro-2-iodo-4-trifluoromethyl-1,3-benzothiazole and conducting the Suzuki coupling at 80° C. for 2 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=9.02-8.92 (brm, 1H), 8.80-8.70 (brm, 1H), 8.58 (dd, J=4.8, 9.2 Hz, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.37 (s, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.17 (brs, 1H), 8.05 (s, 1H), 7.64 (dd, J=9.2, 11.2 Hz, 1H), 4.56-4.47 (mc, 1H), 3.40 (brd, J=12.8 Hz, 2H), 3.11 (brq, J=11.4 Hz, 2H), 2.30-2.11 (m, 4H). MS(ES+): m/z=463.07 (95) [MH+], 380.02 (100) [MH+-piperidine]. HPLC: tR=2.28 min (polar—5 min, ZQ2).

Workup

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

Sources & evidence

ORD record
ord-cecf222cd1a6482bb123a959cbe3ad1a
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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