2-Methoxyethylamine → HCID 57588510, compound

HRID 1782104Notes

Reaction equation

HRID 1782104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([OH:18])=O)[NH:15][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CCN(C(C)C)C(C)C.[CH3:40][O:41][CH2:42][CH2:43][NH2:44]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([NH:44][CH2:43][CH2:42][O:41][CH3:40])=[O:18])[NH:15][C:11]=3[N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 57588501HCID 57588501, compound

Product 1

HCID 57588510HCID 57588510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (70 mg, 0.23 mmol), CDI (75 mg, 0.46 mmol) and DIPEA (0.1 mL) in dry THF (3 mL) was stirred at 60° C. for 1 h and then treated with 2-methoxyethylamine (0.1 mL). After additional 2 h at 60° C., the mixture was concentrated under reduced pressure, the residue suspended in water (5 mL) and the solid collected by filtration and washed with water to give 1-(4-bromophenyl)-N-(2-methoxyethyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxamide EXAMPLE 3. LC-MS (ES+): m/z 363/365 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=3.41 (s, 3H), 3.57 (t, J=4.9 Hz, 2H), 3.67 (app. q, J=4.9 Hz, 2H), 6.34 (br s, 1H, CONH), 6.60 (s, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.64 (d, J=8.7 Hz, 2H), 7.88 (s, 1H), 9.32 (br s, 1H, NH).

Workup

  1. waitAfter additional 2 h at 60° C.
  2. concentrationthe mixture was concentrated under reduced pressure
  3. filtrationthe solid collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-125b9fe47c234e919dab90e1084a743f
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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