2-Chloro-6-methoxybenzothiazole → HCID 67521563, compound

HRID 1926381Notes

Reaction equation

HRID 1926381 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.ClC1SC2C=[C:37]([O:39]C)C=CC=2N=1>>[CH3:37][O:39][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 2731322-Chloro-6-methoxybenzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 67521563HCID 67521563, 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-chloro-6-methoxy-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), 3.04-3.17 (m, 2H), 3.41 (d, J=12.8 Hz, 2H), 3.89 (s, 3H), 4.48-4.59 (m, 1H), 7.20 (dd, J=9.1, 2.5 Hz, 1H), 7.78 (d, J=2.5 Hz, 1H), 8.03 (d, J=9.1 Hz, 1H), 8.08 (s, 1H), 8.38-8.45 (m, 2H), 8.50 (d, J=2.0 Hz, 1H). MS (ES+): m/z=407.12 [MH+]. HPLC: tR=2.13 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-8de968e4b22e4a99b4c29ba30dab3f41
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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