HCID 67520656, compound → 2-[2-Amino-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-benzothiazole-7-carbonitrile

HRID 1926422Notes

Reaction equation

HRID 1926422 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(F)(F)F)=[CH:4][CH:3]=1.I[C:34]1SC2C(C#N)=CC=CC=2[N:38]=1>>[NH2:28][C:12]1[C:11]([C:8]2[S:9][C:10]3[C:2]([C:34]#[N:38])=[CH:3][CH:4]=[CH:5][C:6]=3[N:7]=2)=[CH:16][C:15]([C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:21]=2)=[CH:14][N:13]=1

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 675208322-Iodo-1,3-benzothiazole-7-carbonitrile

Product 1

HCID 675210102-[2-Amino-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-benzothiazole-7-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-iodo-1,3-benzothiazole-7-carbonitrile and conducting the Suzuki coupling at 55° C. for 3 h, the title compound was obtained as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ=2.10-2.31 (m, 4H), 3.05-3.18 (m, 2H), 3.37-3.44 (m, 2H), 3.77 (brs, 2H), 4.45-4.54 (m, 1H), 7.51 (brs, 1H), 7.75-7.78 (m, 1H), 8.07 (d, J=7.2 Hz, 1H), 8.10 (s, 1H), 8.44-8.48 (m, 3H), 8.58 (brs, 1H), 8.88 (brs, 1H), 9.10 (brs, 1H). MS(ES+): m/z=402.13 (100) [MH+]. HPLC: tR=2.06 min (ZQ3, polar—5 min).

Workup

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

Sources & evidence

ORD record
ord-100c3e7bce9d49e3b7b6e3be12da4bf2
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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