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

HRID 1926409Notes

Reaction equation

HRID 1926409 reaction equation
[F:1][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.FC1C2SC(I)=NC=2C=CC=1>>[F:1][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[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]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 675211807-Fluoro-2-iodobenzo[d]thiazole

Product 1

HCID 675204603-(7-Fluorobenzothiazol-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-fluoro-2-iodo-1,3-benzothiazole and conducting the Suzuki coupling at 50° C. for 1.5 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=8.84 (d, J=2.0 Hz, 1H), 8.41 (m, 1H), 8.40 (s, 1H), 8.09 (s, 1H), 8.04 (dd, J=0.8, 8.0 Hz, 1H), 7.66 (m, 1H), 7.38 (m, 1H), 4.66 (m, 1H), 3.62 (dt, J=3.2, 13.2, 2H), 3.24-3.28 (m, 2H), 2.36-2.40 (m, 4H). MS(ES+): m/z=395.12 [MH+]. HPLC: tR=1.62 min (polar—5 min, ZQ3).

Workup

  1. customat 50° C.
  2. customfor 1.5 h

Sources & evidence

ORD record
ord-629ebfe303af4d15b9f3e520aab1be6e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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