HCID 67520656, compound → HCID 67520651, compound

HRID 1926431Notes

Reaction equation

HRID 1926431 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.IC1SC2C=CC([O:43][C:44]([F:47])([F:46])[F:45])=CC=2N=1>>[NH:25]1[CH2:26][CH2:27][CH:22]([N:20]2[CH:21]=[C:17]([C:15]3[CH:16]=[C:11]([C:8]4[S:9][C:10]5[CH:2]=[CH:3][C:4]([O:43][C:44]([F:47])([F:46])[F:45])=[CH:5][C:6]=5[N:7]=4)[C:12]([NH2:28])=[N:13][CH:14]=3)[CH:18]=[N:19]2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 67520656HCID 67520656, compoundHCID 67520943HCID 67520943, compound

Product 1

HCID 67520651HCID 67520651, 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 2-iodo-5-trifluoromethoxy-1,3-benzothiazole and conducting the Suzuki coupling at 50° C. for 2 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=8.84 (d, J=1.6 Hz, 1H), 8.43 (s, 1H), 8.42 (d, J=2.0 Hz, 1H), 8.24 (d, J=8.4 Hz, 1H), 8.15 (m, 1H), 8.09 (s, 1H), 7.55 (m, 1H), 4.68 (m, 1H), 3.61-3.68 (m, 2H), 3.28-3.30 (m, 2H), 2.35-2.42 (m, 4H). MS(ES+): m/z=461.15 [MH+]. HPLC: tR=1.84 min (polar—5 min, ZQ3).

Workup

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

Sources & evidence

ORD record
ord-7fee56472d744e4dac36e1a6b0078a17
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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