1-methyl-1H-1,3-benzodiazole-2-carbaldehyde → 6-[2-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-5,6-dihydro-pyran-2-one

HRID 1453174Notes

Reaction equation

HRID 1453174 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]2([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[O:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=CC=1OC(C)C.[CH3:54][N:55]1[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=2[N:57]=[C:56]1[CH:64]=O.CC1C=C(C)N2N=C(C=O)N=C2N=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]2([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[O:20][C:19](=[O:21])[C:18]([CH2:64][C:56]3[N:55]([CH3:54])[C:59]4[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=4[N:57]=3)=[C:17]([OH:22])[CH2:16]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1

Participants

5

Reactant 4

HCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 167287396-[2-(3-Chloro-4-isopropoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dioneHCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587626706-[2-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione

Product 1

HCID 587623816-[2-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(1-methyl-1H-benzoimidazol-2-ylmethyl)-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared analogously to Example B(31), carbaldehyde where 6-[2-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione was substituted in place of 6-[2-(3-Chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione and 1-methyl-2-formylbenzimidazole was substituted in place of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde of that example. 1H NMR (DMSO-d6): δ 0.10 (d, J=4.7, 2H), 0.33-0.36 (m, 2H), 0.98-2.04 (m, 14H), 2.17-2.26 (m, 2H), 2.29 (d, J=17, 1H), 2.54 (d, J=17 Hz, 1H), 3.56 (s, 3H), 3.60-3.65 (m, 2H), 3.85 (brs, 1H), 6.71-7.26 (m, 7H). Anal. Calcd. For C31H35ClN2O4.0.5H2O: C, 68.43; H, 6.67; N, 5.15. Found: C, 68.36; H, 6.58; N, 4.81. ESIMS (MH+): 536.

Sources & evidence

ORD record
ord-d99d6f1c570f4613b5d33d3877d48b2f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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