Methyl iodide → 4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 873986Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH:16]4[CH2:18][CH2:17]4)=[N:13][NH:12][C:11]=3[C:10](=[O:19])[N:9]2[C:20]2[CH:21]=[C:22]([CH3:30])[C:23]3[N:24]([C:26]([CH3:29])=[N:27][N:28]=3)[CH:25]=2)=[CH:4][CH:3]=1.[CH3:31]I>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:15]3[C:14]([CH:16]4[CH2:18][CH2:17]4)=[N:13][N:12]([CH3:31])[C:11]=3[C:10](=[O:19])[N:9]2[C:20]2[CH:21]=[C:22]([CH3:30])[C:23]3[N:24]([C:26]([CH3:29])=[N:27][N:28]=3)[CH:25]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 178428082HCID 178428082, compound

Product 1

HCID 918263304-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Step 112.5 using 4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 129.1) and MeI at RT for 30 min. The crude product was purified by preparative achiral SFC (column NH2, gradient 19-24% in 6 min_total 11 min). tR: 0.95 min (LC-MS 2); ESI-MS: 433.2 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm-0.10-0.07 (m, 1H) 0.50-0.78 (m, 3H) 1.59-1.76 (m, 1H) 1.92 (s, 3H) 3.36 (s, 3H) 3.92 (s, 3H) 6.09 (s, 1H) 7.27 (d, J=8.4 Hz, 2H) 7.32-7.45 (m, 3H) 7.68 (d, J=2.7 Hz, 1H).

Workup

customThe crude product was purified by preparative achiral SFC (column NH2, gradient 19-24% in 6 min_total 11 min)

Sources & evidence

ORD record: ord-65a3fb20ca26499f860fb2d2069efa04
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975417B2

Reaction notes

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