Triethylamine → HCID 57633126, compound

HRID 2108759Notes

Reaction equation

HRID 2108759 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[C:16]([C:23]2[N:24]=[C:25]([NH2:28])[S:26][CH:27]=2)=[CH:15]1.C(N(CC)CC)C>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:28][C:25]2[S:26][CH:27]=[C:23]([C:16]3[C:17]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=4)[NH:14][CH:15]=3)[N:24]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 39869190HCID 39869190, compound

Product 1

HCID 57633126HCID 57633126, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared from 3-nitrophenyl acetic acid (1 g, 5.52 mmol), N-(1-methanesulfonyl)-benzotriazole (1.5 eq, 1.6 g), 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine and triethylamine (3eq, 2.3 ml) in THF (20 mL) by microwave irradiation at 170° C. for 10 mins as described above. The reaction mixture was concentrated to dryness and CH3CN added. The desired final product was filtered and washed with ether to give clean 2-(3-nitrophenyl)-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide (1.4 g, 66% yield.)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness and CH3CN
  2. additionadded
  3. filtrationThe desired final product was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-53c5d603cf564e8f8bff7523961eadc4
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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