Aniline → HCID 69491192, compound

HRID 1296752Notes

Reaction equation

HRID 1296752 reaction equation
C1(O[C:8](=[O:37])[NH:9][C:10]2[CH:15]=[C:14]([C:16]3[N:20]=[C:19]([CH3:21])[O:18][N:17]=3)[CH:13]=[CH:12][C:11]=2[CH2:22][NH:23][C:24](=[O:36])[C:25]2[CH:30]=C(OC)[C:28]([CH3:33])=[C:27]([O:34][CH3:35])[CH:26]=2)C=CC=CC=1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.Cl[C:46]([O:48][CH3:49])=O>C1COCC1>[CH3:49][O:48][C:46]1[CH:30]=[C:25]([CH:26]=[C:27]([O:34][CH3:35])[C:28]=1[CH3:33])[C:24]([NH:23][CH2:22][C:11]1[CH:12]=[CH:13][C:14]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:15][C:10]=1[NH:9][C:8]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 6115Aniline2×HCID 6586Methyl chloroformateHCID 69639794HCID 69639794, compound

Product 1

HCID 69491192HCID 69491192, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 19a (50 mg, 0.10 mmol) and aniline (0.010 mL, 0.11 mmol) in THF was heated at 60° C. for 5 h. Additional aniline (0.010 mL, 0.11 mmol) was added and the reaction was stirred at rt overnight. Additional methyl chloroformate (0.010 mL, 0.13 mmol) was added and the reaction was stirred at rt for 24 h. The solid precipitate was recovered by filtration and washed with ethyl acetate and MeOH to give compound 19b (13 mg, 26). ESI-MS m/e 502.4 (M+1).

Workup

  1. stirringthe reaction was stirred at rt for 24 h
  2. filtrationThe solid precipitate was recovered by filtration
  3. washwashed with ethyl acetate and MeOH

Sources & evidence

ORD record
ord-d0a5728ed19144f289e8396c71d598ed
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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