2-Thiopheneboronic acid → N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(2-thienyl)phenyl]pyrazolo[1,5-a]pyridin-7-amine

HRID 861129Notes

Reaction equation

HRID 861129 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.[S:35]1[CH:39]=[CH:38][CH:37]=[C:36]1B(O)O>>[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:36]5[S:35][CH:39]=[CH:38][CH:37]=5)[CH:3]=4)[C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH:30]5[CH2:34][CH2:33][CH2:32][CH2:31]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 27339602-Thiopheneboronic acidHCID 10142612HCID 10142612, compound

Product 1

HCID 10208228N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(2-thienyl)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 (200 mg, 0.39 mmol) and thiophene-2-boronic acid, N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[3-(2-thienyl)phenyl]pyrazolo[1,5-a]pyridin-7-amine (84 mg, 42%) was obtained as a yellow foam. 1H NMR (CDCl3): δ 8.00 (d, 1H), 7.95 (s,1H), 7.79 (d, 1H), 7.69 (d, 1H), 7.56 (d, 1H), 7.45 (t, 1H), 7.34–7.27 (m, 3H), 7.09 (m, 1H), 6.39 (d, 1H), 6.17 (m, 2H), 5.16 (m, 1H), 4.35 (m, 1H), 4.01 (m, 1H), 2.16 (m, 4H), 1.82–1.56 (m, 12H); MS m/z 521 (M+1). U16951-72

Sources & evidence

ORD record
ord-6c9c90fa13a64f1aac36f949240e9ec9
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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