HCID 67520656, compound → HCID 67521393, compound

HRID 1926432Notes

Reaction equation

HRID 1926432 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.[Cl:33]C1C2SC(I)=NC=2C(C(F)(F)F)=CC=1>>[Cl: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[C:5]([C:29]([F:32])([F:30])[F:31])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 67520663HCID 67520663, compound

Product 1

HCID 67521393HCID 67521393, 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 7-chloro-2-iodo-4-trifluoromethyl-1,3-benzothiazole and conducting the Suzuki coupling at 70° C. for 3 h, the title compound was obtained as a yellow-green solid. 1H NMR (400 MHz, DMSO-d6): δ=2.14-2.36 (m, 4H), 3.05-3.18 (m, 2H), 3.37-3.44 (m, 2H), 4.01 (brs, 2H), 4.45-4.56 (m, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.99 (d, J=8.4 Hz, 1H), 8.11 (s, 1H), 8.25 (brs, 1H), 8.46 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.62 (d, J=2.4 Hz, 1H), 8.86 (brs, 1H), 9.06 (brs, 1H). MS(ES+): m/z=478.98/481.00 (100/76) [MH+]. HPLC: tR=2.37 min (ZQ3, polar—5 min).

Workup

  1. customat 70° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-aea28010e20743e8a22c4ac8fe64f95d
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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