HCID 67520656, compound → HCID 67520752, compound

HRID 1926437Notes

Reaction equation

HRID 1926437 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=C([O:43][C:44]([F:47])([F:46])[F:45])C=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][CH:4]=[C:5]([O:43][C:44]([F:47])([F:46])[F:45])[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 67521378HCID 67521378, compound

Product 1

HCID 67520752HCID 67520752, 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-4-trifluoromethoxy-1,3-benzothiazole and conducting the Suzuki coupling at 50° C. for 12 h, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=9.12-9.03 (brm, 1H), 8.94-8.82 (brm, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.41 (brs, 2H), 8.34 (very brs, 2H), 8.26 (dd, J=2.2, 6.6 Hz, 1H), 8.07 (s, 1H), 7.66-7.60 (m, 2H), 4.57-4.48 (mc, 1H), 3.41 (brd, J=12.8 Hz, 2H), 3.11 (brq, J=11.2 Hz, 2H), 2.30-2.12 (m, 4H). MS(ES+): m/z=461.06 (74) [MH+], 378.06 (100) [MH+-piperidine]. HPLC: tR=2.27 min (polar—5 min, ZQ2).

Workup

  1. customat 50° C.
  2. customfor 12 h

Sources & evidence

ORD record
ord-e058d53ccce34f94bcb3c45c942d6037
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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