Thiopheneethanamine → HCID 9996522, compound

HRID 736462Notes

Reaction equation

HRID 736462 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.O.ON1C2C=CC=CC=2N=N1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][CH2:29][NH2:30].Cl.CN(C)CCCN=C=NCC>C(#N)C>[NH2:1][C:2]1[C:3]([C:9]([NH:30][CH2:29][CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 116521ThiopheneethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 9996522HCID 9996522, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

A solution of 3-amino-6-bromopyrazine-2-carboxylic acid (0.50 g, 2.3 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949, 2798-2800), 1-hydroxybenzotriazole hydrate (0.41 g, 2.7 mmol) in acetonitrile (5 mL) were added to a stirred solution of 2-thien-2-ylethanamine (0.32 g, 2.5 mmol) in acetonitrile (5 mL) followed by addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.52 g, 2.7 mmol) and acetonitrile (1.5 mL). The resulting mixture was stirred at room temperature over night and the solvent was evaporated. The residue was re-crystallized from acetonitrile and subsequently from methanol to give 0.5 g (66% yield) of the title compound: 1H NMR DMSO-d6, 400 MHz) δ 8.73 (t, J=6 Hz, 1H), 8.34 (s, 1H), 7.71 (br s, 2H), 7.34 (dd, J=5, 1 Hz, 1H), 6.95 (d, J=3 Hz, 1H), 6.91 (m, 1H), 3.50 (q, J=7 Hz, 2H), 3.05 (t, J=7 Hz, 2H); MS (ES) m/z 327 and 329 (M++1).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was re-crystallized from acetonitrile and subsequently from methanol

Sources & evidence

ORD record
ord-632b1e79efc44472a81693125ab4c546
Source dataset
uspto-grants-2009_09
Patent number
US07595321B2

Reaction notes

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