1-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione → 1-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione

HRID 885057Notes

Reaction equation

HRID 885057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2C=NC(C)=[N:10]2)=[C:5]2[NH:15][CH:16]=[C:17]([C:18](=[O:37])[C:19]([N:21]3[CH2:30][CH2:29][C:28]4[C:27]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:26][CH:25]=[N:24][C:23]=4[CH2:22]3)=[O:20])[C:4]=12.Cl.[N:39]1C=CC=[CH:41][C:40]=1C1C2CCNCC=2N=CN=1.COC1C=NC(N2C=CN=N2)=C2NC=C(C(=O)C(O)=O)C=12>>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:41]=[CH:40][N:39]=[N:10]2)=[C:5]2[NH:15][CH:16]=[C:17]([C:18](=[O:37])[C:19]([N:21]3[CH2:30][CH2:29][C:28]4[C:27]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:26][CH:25]=[N:24][C:23]=4[CH2:22]3)=[O:20])[C:4]=12

Participants

4

Reactant 3

HCID 445556641-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dioneHCID 596816242-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidHCID 670725294-(Pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride

Product 1

HCID 445556651-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione

Procedure

The procedure described in Part E of preparation of compound 18 above was employed for the coupling of 4-(pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride with 2-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid to afford 1-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(pyridin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethane-1,2-dione; HRMS: 486.1677 (M+H)+ [calc'd: 486.1684]; 1HNMR (500 MHz, DMSO-d6) δ 12.82 (br s, 1H), 9.18 (s, 2/3H), 9.09 (s, 1/3H), 8.95 (s, 1H), 8.78 (m, 1/3H), 8.68 (m, 2/3H), 8.34 (s, 2/3H), 8.26 (s, 1/3H), 8.12-8.01 (m, 3H), 7.97 (s, 1H), 7.58 (m, 1/3H), 7.53 (m, 2/3H), 4.93 (s, 4/3H), 4.73 (s, 2/3H), 3.96 (s, 1H), 3.93 (m, 2/3H), 3.90 (s, 2H), 3.70 (m, 4/3H), 3.32 (m, 2/3), 3.18 (m, 4/3H).

Sources & evidence

ORD record
ord-575d89ee6a35458487f26518a8025c3b
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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