Octahydropyrrolo(1,2-a)pyrazine → HCID 58883425, compound

HRID 1765315Notes

Reaction equation

HRID 1765315 reaction equation
C(O[C:4]([C:6]1[NH:10][C:9]2[CH:11]=[C:12]([Cl:14])[S:13][C:8]=2[CH:7]=1)=[O:5])C.[CH2:15]1[NH:20][CH2:19][CH2:18][N:17]2[CH2:21][CH2:22][CH2:23][CH:16]12>>[Cl:14][C:12]1[S:13][C:8]2[CH:7]=[C:6]([C:4]([N:20]3[CH2:19][CH2:18][N:17]4[CH2:21][CH2:22][CH2:23][CH:16]4[CH2:15]3)=[O:5])[NH:10][C:9]=2[CH:11]=1

Participants

3

Reactant 2

HCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 11629993332099-38-4

Product 1

HCID 58883425HCID 58883425, compoundYield 30%

Procedure

2-Chloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acid ethyl ester (230 mg, 1.0 mmol) was hydrolyzed (Procedure B) and then coupled with octahydro-pyrrolo[1,2-a]pyrazine (Procedure C) to provide the title compound (93 mg, 30% for two steps) as an off-white solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.4. MS (electrospray): exact mass calculated for C14H16ClN3OS, 309.07; m/z found, 310.1 [M+H]+. 1H NMR (CDCl3, 400 MHz): 10.9 (br s, 1H), 6.86 (s, 1H), 6.64 (d, J=1.4 Hz, 1H), 4.77 (d, J=12.2 Hz, 1H), 4.65 (d, J=12.7 Hz,1H), 3.30-2.90 (m, 4H), 2.30-1.40 (m, 7H).

Sources & evidence

ORD record
ord-74885d5dddfe4bb8adf958e92eb4a1ad
Source dataset
uspto-grants-2007_06
Patent number
US07226938B2

Reaction notes

Loading…