5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 3-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-4-hydroxy-5,6-dihydro-pyran-2-one

HRID 1453243Notes

Reaction equation

HRID 1453243 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH:11]=O)[N:10]=2)[CH:7]=1.CC1C=C(C)N2N=C(C=O)N=C2N=1.[CH:26]1([C:31]2([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([CH:47]([OH:49])[CH3:48])=[C:43]([F:50])[CH:42]=3)[O:36][C:35](=[O:37])[CH2:34][C:33](=[O:38])[CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27]1.ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=C(CC)C=1OC>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH2:11][C:34]3[C:35](=[O:37])[O:36][C:31]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)([CH2:39][CH2:40][C:41]4[CH:46]=[CH:45][C:44]([CH:47]([OH:49])[CH3:48])=[C:43]([F:50])[CH:42]=4)[CH2:32][C:33]=3[OH:38])[N:10]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587622136-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dioneHCID 587625546-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 688687366-Cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-dihydro-pyran-2,4-dione

Product 1

HCID 688659603-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-4-hydroxy-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example B(97) where where 6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde and 6-Cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-dihydro-pyran-2,4-dione (Example B(115) (was substituted in place of 6-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dione of that example. 1H NMR (400 MHz, DMSO-d6): δ 1.13 (d, J=6.4 Hz, 3H), 1.23-1.60 (m, 8H), 1.81-1.91 (m, 2H), 2.21-2.25 (m, 1H), 2.40-2.46 (m 3H), 2.6 (d, J=16 Hz, 1H), 3.14 (s, 1H), 3.58 (d, J=16 Hz, 1H), 3.68 (d, J=16 Hz, 1H), 4.78-4.80 (m, 1H), 5.02 (d, J=5 Hz, 1H), 6.75 (d, J=10 Hz, 1H), 6.85 (d, J=7.7 Hz, 1H), 7.23 (t, J=7.70 Hz, 1H), 8.70 (d, J=2.5 Hz, 1H), 9.4 (d, J=2.5 Hz, 1H). Anal. Calcd. For C26H28ClFN4O4.0.5H2O: C, 59.60; H, 5.58; N, 10.69. Found: C, 59.67; H, 5.44; N, 10.65. MS (ESI): 515.2 (M+H)+.

Sources & evidence

ORD record
ord-09a2053138c541d88d14fecc2d8d041f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…