2-Chloro-4-bromobenzothiazole → HCID 44158934, compound

HRID 1926399Notes

Reaction equation

HRID 1926399 reaction equation
F[C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH:19]=4)[CH:14]=3)[S:8][C:4]=2[CH:3]=1.[Br:29]C1C2N=C(Cl)SC=2C=CC=1>>[Br:29][C:27]1[C:5]2[N:6]=[C:7]([C:9]3[C:10]([NH2:26])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[N:17][N:18]([CH:20]5[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]5)[CH:19]=4)[CH:14]=3)[S:8][C:4]=2[CH:3]=[CH:2][CH:28]=1

Participants

3

Reactant 2

HCID 20498652-Chloro-4-bromobenzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 44158934HCID 44158934, compound

Procedure

Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 4-bromo-2-chloro-1,3-benzothiazole in place of 2-chloro-6-fluorobenzothiazole to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=8.81 (s, 1H), 8.44 (s, 1H), 8.41 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 8.08 (s, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.47 (t, J=8.0 Hz, 1H), 4.68 (m, 1H), 3.59-3.63 (m, 2H), 2.38-2.41 (m, 4H). MS(ES+): m/z=455.01/456.92 [MH+]. HPLC: tR=1.59 min (polar—5 min, ZQ3).

Sources & evidence

ORD record
ord-8bd00969161f4f639522115fa3fb5e4e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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