Octahydropyrrolo(1,2-a)pyrazine → HCID 58883420, compound

HRID 1765310Notes

Reaction equation

HRID 1765310 reaction equation
[S:1]1[C:5]2[NH:6][C:7]([C:9]([OH:11])=O)=[CH:8][C:4]=2[CH:3]=[CH:2]1.[CH2:12]1[NH:17][CH2:16][CH2:15][N:14]2[CH2:18][CH2:19][CH2:20][CH:13]12>>[CH2:12]1[N:17]([C:9]([C:7]2[NH:6][C:5]3[S:1][CH:2]=[CH:3][C:4]=3[CH:8]=2)=[O:11])[CH2:16][CH2:15][N:14]2[CH2:18][CH2:19][CH2:20][CH:13]12

Participants

3

Reactant 2

HCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 116223946H-thieno[2,3-b]pyrrole-5-carboxylic acid

Product 1

HCID 58883420HCID 58883420, compoundYield 35%

Procedure

6H-Thieno[2,3-b]pyrrole-5-carboxylic acid (60 mg, 0.35 mmol) was coupled with octahydro-pyrrolo[1,2-a]pyrazine according to Procedure C to provide the title compound (34 mg, 35%) as a light yellow solid. TLC (silica, 10% MeOH/CH2Cl2): Rf=0.4. MS (electrospray): exact mass calculated for C14H17N3OS, 275.11; m/z found, 276.2 [M+H]+. 1H NMR (CDCl3, 400 MHz): 11.1 (br s, 1H), 6.96 (d, J=5.4 Hz, 1H), 6.87 (d, J=5.4 Hz, 1H), 6.71 (d, J=1.9 Hz, 1H), 4.84 (d, J=12.2 Hz, 1H), 4.70 (d, J=12.2 Hz, 1H), 3.30-2.90 (m, 4H), 2.30-1.40 (m, 7H).

Sources & evidence

ORD record
ord-1c6690b124ff4ed5814ab5c3056c2fe8
Source dataset
uspto-grants-2007_06
Patent number
US07226938B2

Reaction notes

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