2-Morpholinoethylamine → HCID 10426742, compound

HRID 736461Notes

Reaction equation

HRID 736461 reaction equation
Cl.CN(C)CCCN=C=NCC.[N:13]1([CH2:19][CH2:20][NH2:21])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[NH2:22][C:23]1[C:24]([C:30](O)=[O:31])=[N:25][C:26]([Br:29])=[CH:27][N:28]=1.O.ON1C2C=CC=CC=2N=N1>C(#N)C>[NH2:22][C:23]1[C:24]([C:30]([NH:21][CH2:20][CH2:19][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:31])=[N:25][C:26]([Br:29])=[CH:27][N:28]=1

Participants

6

Reactant 4

HCID 4082852-MorpholinoethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 10426742HCID 10426742, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.68 g, 3.5 mmol) was added in one portion to a stirred suspension of 2-morpholin-4-ylethanamine (0.422 g, 3.2 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (0.64 g, 3.0 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949, 2798-2800), and 1-hydroxybenzotriazole hydrate (0.48 g, 3.5 mmol) in acetonitrile (25 mL) at 0° C. The cooling bath was removed and stirring was continued at room temperature for 7 h. The solid was filtered off, washed with acetonitrile and purified by column chromatography on silica using methylene chloride/methanol/triethyl amine, (95:5:0.1), to give 0.68 g (69% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 8.53 (m, 1H), 8.34 (s, 1H), 8.68 (br s, 2H), 3.57 (t, J=5 Hz, 4H), 3.37 (q, J=7 Hz, 2H), 2.47 (q, J=7 Hz, 2H), 2.40 (m, 4H); MS (ES) m/z 330 and 332 (M++1).

Workup

  1. customThe cooling bath was removed
  2. filtrationThe solid was filtered off
  3. washwashed with acetonitrile
  4. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-29e8b1586a2b42fba52813edb692025e
Source dataset
uspto-grants-2009_09
Patent number
US07595321B2

Reaction notes

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