Octahydropyrrolo(1,2-a)pyrazine → HCID 58883424, compound

HRID 1765311Notes

Reaction equation

HRID 1765311 reaction equation
C(O[C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([Cl:14])=[CH: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:11][C:9]2[NH:10][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])=[CH:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 116010652-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester

Product 1

HCID 58883424HCID 58883424, compoundYield 78%

Procedure

2-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (102 mg, 0.45 mmol) was hydrolyzed (Procedure B) and then coupled with octahydro-pyrrolo[1,2-a]pyrazine (Procedure D) to provide the title compound (108 mg, 78% for two steps) as an off-white solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.35. MS (electrospray): exact mass calculated for C14H16ClN3OS, 309.07; m/z found, 310.1 [M+H]+. 1H NMR (CDCl3, 400 MHz): 11.1 (br s, 1H), 6.86 (s, 1H), 6.62 (s, 1H), 4.79 (d, J=11.8 Hz, 1H), 4.67 (d, J=11.8 Hz, 1H), 3.30-2.90 (m, 4H), 2.30-1.40 (m, 7H).

Sources & evidence

ORD record
ord-3f0f82058c604337a48a03acc5c85724
Source dataset
uspto-grants-2007_06
Patent number
US07226938B2

Reaction notes

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