HCID 67520656, compound → 2-[2-Amino-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-benzothiazole-4-carbonitrile

HRID 1926434Notes

Reaction equation

HRID 1926434 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)(F)F)=[CH:4][CH:3]=1.ClC1SC2C(=C(C#N)C=CC=2)[N:38]=1>>[NH2:28][C:12]1[C:11]([C:8]2[S:9][C:10]3[C:6](=[C:5]([C:29]#[N:38])[CH:4]=[CH:3][CH:2]=3)[N:7]=2)=[CH:16][C:15]([C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH:21]=2)=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 675209882-Chlorobenzo[d]thiazole-4-carbonitrile

Product 1

HCID 675212422-[2-Amino-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-benzothiazole-4-carbonitrile

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 2-chloro-1,3-benzothiazole-4-carbonitrile and conducting the Suzuki coupling at 80° C. for 2 h, the title compound was obtained as a yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ=2.04-2.23 (m, 4H), 3.04 (m, 2H), 3.30 (m, 2H), 4.44 (mc, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.99 (s, 1H), 8.03 (dd, J=7.6, 1.0 Hz, 1H), 8.34 (s, 1H), 8.49 (dd, J=8.1, 1.0 Hz, 1H), 8.51 (d, J=2.3 Hz, 1H), 8.86 (broad s, 1H), 9.03 (broad s, 1H). MS (ES′): m/z=402.15 [MH+]. HPLC: tR=2.28 min (ZQ3, polar—5 min).

Workup

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

Sources & evidence

ORD record
ord-b3b3612ef3d24510951bdeb3a842cce9
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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