N-{5-[3-(2-chloropyrimidin-4-yl)pyrazolo[1,5-a]pyridin-2-yl]-2-methoxyphenyl}-2-(2-thienyl)acetamide → N-[3-(3-{2-[(7-Amino-5,6,7,8-tetrahydro-2-naphthalenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamide

HRID 1157642Notes

Reaction equation

HRID 1157642 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20](OC)=[C:21]([NH:23][C:24](=[O:31])[CH2:25][C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.Cl.Cl.CN(C)CCO[C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44]>>[NH2:7][CH:6]1[CH2:8][C:41]2[CH:42]=[C:43]([NH:44][C:2]3[N:7]=[C:6]([C:8]4[C:9]([C:17]5[CH:22]=[C:21]([NH:23][C:24](=[O:31])[CH2:25][C:26]6[S:27][CH:28]=[CH:29][CH:30]=6)[CH:20]=[CH:19][CH:18]=5)=[N:10][N:11]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=45)[CH:5]=[CH:4][N:3]=3)[CH:45]=[CH:46][C:47]=2[CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57737232N-{5-[3-(2-chloropyrimidin-4-yl)pyrazolo[1,5-a]pyridin-2-yl]-2-methoxyphenyl}-2-(2-thienyl)acetamideHCID 66649609[2-(3-Aminophenoxy)ethyl]dimethylamine dihydrochloride

Product 1

HCID 57737171N-[3-(3-{2-[(7-Amino-5,6,7,8-tetrahydro-2-naphthalenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2-(2-thienyl)acetamideYield 64.4%

Procedure

N-[5-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)phenyl]-2-(2-thienyl)acetamide (119 mg, 0.25 mmol) and 3-{[2-(dimethylamino)ethyl]oxy}-aniline dihydrochloride (127 mg, 0.50 mmol) were coupled according to the procedure of Example 56, Step H to give the title compound (46 mg, 30%). 1H NMR (400 MHz, d6-DMSO) δ 8.80 (s, 1H), 8.48 (d, J=7.2 Hz, 1H), 8.35 (d, J=9.2 Hz, 1H), 8.16 (d, J=5.2 Hz, 1H), 8.01 (s, 1H), 7.49 (s, 1H), 7.28-7.24 (m, 4H), 7.22-7.18 (m, 1H), 7.12 (d, J=8.4 Hz, 1H), 7.04-7.03 (m, 2H), 6.89-6.86 (m, 2H), 6.61-6.59 (m, 2H), 4.09 (m, 2H), 3.95 (s, 2H), 3.81 (s, 3H), 2.76 (m, 2H), 2.35 (s, 6H) ppm. ES-LC/MS m/z=620 [M+H]+.

Sources & evidence

ORD record
ord-8a164179fe654d25b80ec07bba26a5d0
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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