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

HRID 244038Notes

Reaction equation

HRID 244038 reaction equation
N1N=C(C2C=CC=CC=2C([N:14]2[CH2:18][CH:17]3[CH2:19][N:20]([C:22](OC(C)(C)C)=O)[CH2:21][CH:16]3[CH2:15]2)=O)NC=1.C(OC(N1CC2C(CNC2)C1)=O)(C)(C)C.[F:44][C:45]1[CH:53]=[CH:52][CH:51]=[C:50]([N:54]2[N:58]=[CH:57][CH:56]=[N:55]2)[C:46]=1[C:47]([OH:49])=O.[N:59]1[N:60]=[C:61]([C:64]2C=CC=CC=2C(O)=O)[NH:62][CH:63]=1>>[F:44][C:45]1[CH:53]=[CH:52][CH:51]=[C:50]([N:54]2[N:58]=[CH:57][CH:56]=[N:55]2)[C:46]=1[C:47]([N:14]1[CH2:15][CH:16]2[CH:17]([CH2:19][N:20]([C:22]3[N:60]=[C:61]([CH3:64])[N:62]=[CH:63][N:59]=3)[CH2:21]2)[CH2:18]1)=[O:49]

Participants

5

Reactant 4

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 178451519HCID 178451519, compoundHCID 178524291HCID 178524291, compound

Product 1

HCID 671162092-{[2-Fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-5-(4-methyl-1,3,5-triazin-2-yl)octahydropyrrolo[3,4-c]pyrrole

Procedure

Example 303 was prepared in a manner analogous to Intermediate 59 substituting the product of Step C for Intermediate 15 and Intermediate 12 for 2-(4H-[1,2,4]triazol-3-yl)-benzoic acid. MS (ESI) mass calculated for C19H19FN8O, 394.41; m/z found, 395.0. 1H NMR (500 MHz, CDCl3): 8.51-8.42 (m, 1H), 7.89-7.81 (m, 2H), 7.75 (d, J=3.5 Hz, 1H), 7.54-7.45 (m, 1H), 7.20-7.11 (m, 1H), 4.02-3.51 (m, 8H), 3.32-3.23 (m, 1H), 3.17-3.00 (m, 2H), 2.50-2.40 (m, 3H).

Sources & evidence

ORD record
ord-a801c245a8124828aa377a934b655651
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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