2-Methoxyethylamine → HCID 59185795, compound

HRID 1951249Notes

Reaction equation

HRID 1951249 reaction equation
N1C=CC=NC=1.[CH3:7][C:8]1[N:12]2[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:11]2=[C:10]([CH3:18])[C:9]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=O)=[CH:28][CH:27]=2)[N:20]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:57][O:58][CH2:59][CH2:60][NH2:61]>C1COCC1.O>[CH3:7][C:8]1[N:12]2[CH2:13][CH2:14][NH:15][C:16](=[O:17])[C:11]2=[C:10]([CH3:18])[C:9]=1[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:61][CH2:60][CH2:59][O:58][CH3:57])=[O:35])=[CH:30][CH:31]=2)[N:20]=1

Participants

8

Reactant 5

HCID 80182-MethoxyethylamineHCID 9260PyrimidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 16666039HCID 16666039, compound

Product 1

HCID 59185795HCID 59185795, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the pyrimidine acid Example I-70 {4-[4-(6,8-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazin-7-yl)-pyrimidin-2-ylamino]-phenyl}-acetic acid (0.05 g), EDCI (1.2 eq., 0.028 g) and HOBt (1.2 eq., 0.02 g) in THF (3 mL) was stirred at room temperature under nitrogen for 1 hour. 2-Methoxyethylamine (1.2 eq., 0.013 mL) was then added and the resulting reaction stirred at room temperature for 16 hours. Water (5 mL) was added and the solvent removed under vacuum to leave an aqueous suspension which was extracted with dichloromethane (2×2 mL). The combined organics were stripped to yield the crude product as a yellow oil (0.0656 g). Purification of the crude material (prep. HPLC) produced the title compound as a white solid (0.0269 g, 47%, with a purity of 98.37% by LCMS.

Workup

  1. customthe resulting reaction
  2. customthe solvent removed under vacuum
  3. customto leave an aqueous suspension which
  4. extractionwas extracted with dichloromethane (2×2 mL)
  5. customto yield the crude product as a yellow oil (0.0656 g)
  6. customPurification of the crude material (prep. HPLC)

Sources & evidence

ORD record
ord-64a6a6df732443ed96bc2e12e056a84b
Source dataset
uspto-grants-2013_03
Patent number
US08404692B2

Reaction notes

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