HCID 67520656, compound → HCID 44159050, compound

HRID 1926433Notes

Reaction equation

HRID 1926433 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)F)=C[CH:3]=1.FC1C=CC2SC(I)=NC=2C=1>>[F:32][C:29]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 67520969HCID 67520969, compound

Product 1

HCID 44159050HCID 44159050, 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-1,3-benzothiazole and conducting the Suzuki coupling at 55° C. for 3 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=9.20-9.09 (brm, 1H), 9.04-8.92 (brm, 1H), 8.71 (very brs, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.55 (brs, 1H), 8.47 (s, 1H), 8.28 (dd, J=5.2, 9.0 Hz, 1H), 8.10 (s, 1H), 8.01 (dd, J=2.6, 9.4 Hz, 1H), 7.47 (dt, J=2.4, 9.0 Hz, 1H), 4.58-4.48 (mc, 1H), 3.40 (brd, J=12.5 Hz, 2H), 3.11 (brq, J=12.0 Hz, 2H), 2.30-2.12 (m, 4H). MS(ES+): m/z=395.09 (73) [MH+], 312.05 (100) [MH+-piperidine]. HPLC: tR=2.06 min (polar—5 min, ZQ2).

Workup

  1. customat 55° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-0d6a0ce21ed24ab7bad3498941243090
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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