2,6-Dichlorobenzothiazole → HCID 67520693, compound

HRID 1926379Notes

Reaction equation

HRID 1926379 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.[Cl:29]C1SC2C=C(Cl)C=CC=2N=1>>[Cl:29][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

Participants

3

Reactant 2

HCID 771762,6-DichlorobenzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 67520693HCID 67520693, compound

Procedure

Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 2,6-dichloro-1,3-benzothiazole in place of 2-chloro-6-fluorobenzothiazole to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.10-2.30 (m, 4H), 3.06-3.18 (m, 2H), 3.41 (d, J=13.2 Hz, 2H), 4.52 (ddd, J=14.8, 10.6, 4.2 Hz, 1H), 7.62 (dd, J=8.8, 1.8 Hz, 1H), 8.05 (s, 1H), 8.12 (d, J=8.8 Hz, 1H), 8.31 (br. s., 1H), 8.37 (br. s., 2H), 8.53 (s, 1H). MS (ES+): m/z=411.08 [MH+]. HPLC: tR=2.30 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-4f8e5c2492fa4ff8a277eda302cfbb75
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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