2-Chloro-7-methyl-1,3-benzothiazole → 3-(7-Methylbenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1926395Notes

Reaction equation

HRID 1926395 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[C:30]1SC2C(C)=CC=CC=2N=1>>[CH3:30][C:3]1[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]=[CH:28][CH:2]=1

Participants

3

Reactant 2

HCID 552764852-Chloro-7-methyl-1,3-benzothiazoleHCID 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 441589323-(7-Methylbenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

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-7-methyl-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=2.11-2.31 (m, 4H), 2.61 (s, 3H), 3.12 (q, J=11.8 Hz, 2H), 3.42 (d, J=12.8 Hz, 2H), 4.46-4.56 (m, 1H), 7.36 (d, J=7.3 Hz, 1H), 7.52 (t, J=7.7 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H), 8.07 (s, 1H), 8.43 (br. s., 2H), 8.52 (s, 1H). MS (ES+): m/z=391.16 [MH+]. HPLC: tR=2.24 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-4dcf496a8e30437ebbdb566121c76267
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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