Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate → 2-(4,6-Dimethylpyrimidin-2-yl)-5-{[2-fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

HRID 244044Notes

Reaction equation

HRID 244044 reaction equation
N1N=C(C2C=CC=CC=2C(N2CC3CN(C(OC(C)(C)C)=O)CC3C2)=O)NC=1.[CH3:29][C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([N:37]2[CH2:44][CH:43]3[CH:39]([CH2:40][NH:41][CH2:42]3)[CH2:38]2)[N:31]=1.C(OC(N1CC2C(CNC2)C1)=O)(C)(C)C.[F:60][C:61]1[CH:69]=[CH:68][CH:67]=[C:66]([C:70]2[O:74][N:73]=[C:72]([CH3:75])[N:71]=2)[C:62]=1[C:63](O)=[O:64].N1N=C(C2C=CC=CC=2C(O)=O)NC=1>>[CH3:29][C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([N:37]2[CH2:44][CH:43]3[CH:39]([CH2:40][N:41]([C:63]([C:62]4[C:66]([C:70]5[O:74][N:73]=[C:72]([CH3:75])[N:71]=5)=[CH:67][CH:68]=[CH:69][C:61]=4[F:60])=[O:64])[CH2:42]3)[CH2:38]2)[N:31]=1

Participants

6

Reactant 5

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 662108752-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrroleHCID 670868322-Fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 178451519HCID 178451519, compoundHCID 178524291HCID 178524291, compound

Product 1

HCID 671168302-(4,6-Dimethylpyrimidin-2-yl)-5-{[2-fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

Procedure

The title compound was prepared in a manner analogous to Intermediate 59 substituting Intermediate 23 for Intermediate 15 and Intermediate 64 for 2-(4H-[1,2,4]triazol-3-yl)-benzoic acid. MS (ESI) mass calculated for C22H23FN6O2, 422.19; m/z found, 423.2. 1H NMR (500 MHz, CDCl3): 7.96-7.86 (m, 1H), 7.55-7.47 (m, 1H), 7.38-7.29 (m, 1H), 6.32-6.23 (m, 1H), 3.99-3.46 (m, 7H), 3.27-2.95 (m, 3H), 2.49-2.37 (m, 3H), 2.36-2.21 (m, 6H).

Sources & evidence

ORD record
ord-eb7cb7179af5414cab9b5ff3541da1d6
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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