2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → 5-(2-benzyl-2H-indazol-6-yl)-7-Piperidin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972920Notes

Reaction equation

HRID 1972920 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][N:12]3C(OC(C)(C)C)=O)[N:6]2[N:5]=[CH:4][N:3]=1.[CH2:24]([N:31]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35](B3OC(C)(C)C(C)(C)O3)[CH:36]=[CH:37]2)=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([N:31]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([C:8]3[CH:9]=[C:10]([CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:36]=[CH:37]2)=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 69303264HCID 69303264, compound

Product 1

HCID 693035755-(2-benzyl-2H-indazol-6-yl)-7-Piperidin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine

Procedure

Following the procedure described in Steps 3-5 (bromination, coupling, deprotection) of Example 1, the title compound was prepared using tert-butyl 2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate and Intermediate C. 1H NMR (400 MHz, CD3OD) δ 8.36 (s, 1 H), 7.85 (s, 1 H), 7.81 (d, 1 H), 7.64 (s, 1 H), 7.27-7.41 (m, 5 H), 7.22 (dd, 1 H), 6.73 (s, 1 H), 5.65 (s, 2 H), 4.27 (dd, 1 H), 3.08-3.18 (m, 1 H), 2.79-2.90 (m, 1 H), 1.51-2.14 (m, 6 H); ES-MS m/z 424.42 [M+H]+, HPLC RT (min) 2.14.

Sources & evidence

ORD record
ord-bb5fe51ab59a4dd5b6b3d2d73d13289c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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