2,5-Dichloro-1,3-benzothiazole → HCID 44158820, compound

HRID 1926384Notes

Reaction equation

HRID 1926384 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=CC(Cl)=CC=2N=1>>[Cl:29][C:28]1[CH:2]=[CH:3][C:4]2[S:8][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)=[N:6][C:5]=2[CH:27]=1

Participants

3

Reactant 2

HCID 133148162,5-Dichloro-1,3-benzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 44158820HCID 44158820, compound

Procedure

Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 2,5-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=2.10-2.22 (m, 2H), 2.22-2.30 (m, 2H), 3.12 (q, J=11.1 Hz, 2H), 3.42 (d, J=12.4 Hz, 2H), 4.47-4.55 (m, 1H), 7.56 (d, J=8.4 Hz, 1H), 8.03 (s, 1H), 8.19-8.24 (m, 2H), 8.26 (br. s., 1H), 8.35 (s, 1H), 8.52 (s, 1H), MS (ES+): m/z=411.09/413.10 (3:1) [MH+]. HPLC: tR=2.18 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-fe5c33a815604beba2a09794a815bbe0
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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