4-Methylmorpholine → HCID 20677652, compound

HRID 650666Notes

Reaction equation

HRID 650666 reaction equation
CN1CCOCC1.[Br:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1.Cl.Cl.[CH3:19][O:20][C:21](=[O:32])[CH:22]([NH:25][C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:23][NH2:24].ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:19][O:20][C:21](=[O:32])[CH:22]([NH:25][C:26]1[N:27]=[CH:28][CH:29]=[CH:30][N:31]=1)[CH2:23][NH:24][C:14]([C:12]1[S:13][C:9]([Br:8])=[CH:10][CH:11]=1)=[O:16]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 3491155-Bromothiophene-2-carboxylic acidHCID 70095140HCID 70095140, compound

Product 1

HCID 20677652HCID 20677652, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methylmorpholine (0.23 mL, 2.10 mmol) was added to a mixture of 5-bromothiophene-2-carboxylic acid (124 mg, 0.60 mmol), 3-amino-2-(pyrimidin-2-ylamino)-propionic acid methyl ester bis-hydrochloride salt (161 mg, 0.60 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarboiimide hydrochloride (115 mg, 0.60 mmol) and 1-hydroxybenzotriazole (81 mg, 0.60 mmol) in dry DMF (2 mL). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated, solvent removed in vacuo and the residue chromatographed. Elution with 5% methanol in dichloromethane gave compound G-2 as a yellow foam (186 mg, 81% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customsolvent removed in vacuo
  3. customthe residue chromatographed
  4. washElution with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-567079f14f8544fea1b13945f25d4a22
Source dataset
uspto-grants-2001_08
Patent number
US06274620B1

Reaction notes

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