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Triethylamine → HCID 178492298, compound

HRID 857888
Notes
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Reaction equation

HRID 857888 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C[Al](C)C.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:47](=[N:55][C:56]#[N:57])OC2C=CC=CC=2)=[CH:42][CH:41]=1>ClCCl.C1(C)C=CC=CC=1>[C:56]([N:55]=[C:47]([NH:46][C:43]1[CH:44]=[CH:45][C:40]([O:39][CH3:38])=[CH:41][CH:42]=1)[N:15]1[CH2:14][CH2:13][N:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([Cl:8])[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16]1)#[N:57]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 16682925TrimethylaluminumHCID 68886670HCID 68886670, compoundHCID 178492300N-4-methoxyphenyl-N'-cyano-O-phenylisourea

Product 1

HCID 178492298HCID 178492298, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (100 mg, Reference Example 1) in dry dichloromethane (2 mL) under a blanket of nitrogen was treated with dry triethylamine (35 μL), then with a 2M solution of trimethylaluminum in toluene (0.30 mL) dropwise. After stirring at room temperature for a further 30 minutes the reaction mixture was treated with N-4-methoxyphenyl-N′-cyano-O-phenylisourea (64 mg, Reference Example 46) and then further stirred at room temperature for 3 hours. The reaction mixture was then heated overnight at 50° C. and then allowed to cool to room temperature. The reaction mixture was further treated with dichloromethane and then washed with a 0.5M aqueous solution of sodium carbonate. The organic phase was dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of pentane and ethyl acetate (1:1, v/v) then ethyl acetate to give 2-[(cyanoimino)(4-methoxyphenylamino)methyl]-7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (10 mg) as a white solid, m.p. 170° C. MS: 451 [MH]+, 449 [MH]+.

Workup

  1. stirringfurther stirred at room temperature for 3 hours
  2. temperatureThe reaction mixture was then heated overnight at 50° C.
  3. temperatureto cool to room temperature
  4. washwashed with a 0.5M aqueous solution of sodium carbonate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. additionThe residue was subjected to column chromatography on silica eluting with a mixture of pentane and ethyl acetate (1:1

Sources & evidence

ORD record
ord-47cb7cb2a9ee47db884a41477511e2ce
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07148215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes