(Pyridin-4-yl)boronic acid → N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(4-pyridinyl)phenyl]pyrazolo[1,5-a]pyridin-7-amine

HRID 861127Notes

Reaction equation

HRID 861127 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:24]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH:16][CH:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>>[CH:17]1([NH:16][C:15]2[N:10]3[N:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([C:38]5[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=5)[CH:3]=4)[C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:31][CH2:32][CH2:33][CH2:34]5)[N:24]=4)=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 10142612HCID 10142612, compound

Product 1

HCID 10164744N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(4-pyridinyl)phenyl]pyrazolo[1,5-a]pyridin-7-amineYield 42%

Procedure

In a similar manner as described in Example 29 from 2-(3-bromophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (100 mg, 0.19 mmol) and pyridine-4-boronic acid, N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(4-pyridinyl)phenyl]pyrazolo[1,5-a]pyridin-7-amine (41 mg, 42%) was obtained as a yellow foam. 1H NMR (CDCl3): δ 8.66 (d, 2H), 8.02 (d, 1H), 7.96 (s, 1H), 7.76–7.69 (m, 3H), 7.58–7.51 (m, 3H), 7.33 (t, 1H), 6.36 (d, 1H), 6.06–6.04 (m, 2H), 5.15 (m, 1H), 4.32 (m, 1H), 4.01 (m, 1H), 2.17–2.03 (m, 4H), 1.81–1.52 (m, 12H); MS m/z 516 (M+1).

Sources & evidence

ORD record
ord-dc2dfb5143a74c649df97b988c8b7e6b
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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