3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine → HCID 67521036, compound

HRID 1926425Notes

Reaction equation

HRID 1926425 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]C1C=CC2SC(I)=NC=2C=1>>[Br: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 675210153-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamineHCID 67521227HCID 67521227, compound

Product 1

HCID 67521036HCID 67521036, compound

Procedure

Same procedure as 3-(6-fluorobenzothiazol-2-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine except using 5-bromo-2-iodo-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=2.11-2.30 (m, 4H), 3.11 (q, J=11.0 Hz, 2H), 3.41 (d, J=12.8 Hz, 2H), 4.47-4.56 (m, 1H), 7.74 (dd, J=8.6, 2.0 Hz, 1H), 8.03-8.08 (m, 2H), 8.34 (br. s., 1H), 8.39 (s, 1H), 8.51 (d, J=1.4 Hz, 1H), 8.54 (d, J=2.2 Hz, 1H). MS (ES+): m/z=455.02/457.00 [MH+]. HPLC: tR=2.19 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-3cc0da3730df4ed2afd2e3255f295f95
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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