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

HRID 244042Notes

Reaction equation

HRID 244042 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.[CH3:60][C:61]1[N:65]=[C:64]([C:66]2[CH:74]=[CH:73][CH:72]=[CH:71][C:67]=2[C:68](O)=[O:69])[O:63][N:62]=1.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:68]([C:67]4[CH:71]=[CH:72][CH:73]=[CH:74][C:66]=4[C:64]4[O:63][N:62]=[C:61]([CH3:60])[N:65]=4)=[O:69])[CH2:42]3)[CH2:38]2)[N:31]=1

Participants

6

Reactant 5

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acidHCID 662108752-(4,6-Dimethylpyrimidin-2-yl)octahydropyrrolo[3,4-c]pyrroleHCID 178451519HCID 178451519, compoundHCID 178524291HCID 178524291, compound

Product 1

HCID 671166272-(4,6-Dimethylpyrimidin-2-yl)-5-{[2-(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 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid for 2-(4H-[1,2,4]triazol-3-yl)benzoic acid. MS (ESI) mass calculated for C22H24N6O2, 404.48; m/z found, 405.2. 1H NMR (500 MHz, CDCl3): 8.10 (dd, J=7.9 Hz, 0.9 Hz, 1H), 7.62 (td, J=7.6 Hz, 1.2 Hz, 1H), 7.53 (td, J=7.7 Hz, 1.3 Hz, 1H), 7.42 (dd, J=7.6 Hz, 1.0 Hz, 1H), 6.28 (s, 1H), 3.99-3.88 (m, 2H), 3.80-3.75 (m, 1H), 3.74-3.65 (m, 2H), 3.53-3.48 (m, 1H), 3.46-3.40 (m, 1H), 3.12-3.04 (m, 2H), 3.01-2.93 (m, 1H), 2.42 (s, 3H), 2.28 (s, 6H).

Sources & evidence

ORD record
ord-f8b7b20a2c024581b19496732d464a91
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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