Ethylmorpholine → N-(3-Chlorophenyl)-1-ethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

HRID 733747Notes

Reaction equation

HRID 733747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH2:18][CH3:19])[C:13]=3[C:12]([C:20](O)=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C(N1CCOCC1)C>CN(C)C=O.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH2:18][CH3:19])[C:13]=3[C:12]([C:20]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 578410324-[(3-Chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

Product 1

HCID 11581787N-(3-Chlorophenyl)-1-ethyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(3-chlorophenyl)amino]-1-ethyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (20 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15 mg), 1-hydroxybenzotriazole hydrate (11 mg), morpholine (11 ul) and N-ethylmorpholine (32 ul) in dimethylformamide (2 ml) was stirred under argon over night. The reaction mixture was diluted with diethyl ether and washed with water. The aqueous layer was acidified with an aqueous 2M hydrochloric acid solution and then extracted three times with diethyl ether. The combined organic layers were washed with brine, dried (MgSO4) and evaporated to afford the title compound as a yellow oil (14 mg).

Workup

  1. washwashed with water
  2. extractionextracted three times with diethyl ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a73aa566d1dd40de9803d3f5bdc6e0f0
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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