Ethylmorpholine → HCID 68867151, compound

HRID 733739Notes

Reaction equation

HRID 733739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][NH:17][C:13]=3[C:12]([C:18]([OH:20])=[O:19])=[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:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(N1CCOCC1)C>CN(C)C=O.C(OCC)C>[CH:18]([OH:20])=[O:19].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][NH:17][C:13]=3[C:12]([C:18]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:20])=[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 57840839HCID 57840839, compound

Product 1

HCID 68867151HCID 68867151, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(3-chlorophenyl)amino]-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (175 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), 1-hydroxybenzotriazole hydrate (108 mg), morpholine (106 ul) and N-ethylmorpholine (309 ul) in dimethylformamide (3 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 a brown oil. Purification by MDAP afforded the title compound as a clear oil (86 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
  6. customto afford a brown oil
  7. customPurification by MDAP

Sources & evidence

ORD record
ord-288a71e655fd45cd94628a7fcaee0e29
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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