Indole-3-Acetic Acid → HCID 69338298, compound

HRID 1179085Notes

Reaction equation

HRID 1179085 reaction equation
CN1CCOCC1.[Cl:8]C1N=C(OC)N=C(OC)N=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29]([OH:31])=O)=[CH:20]1.[CH3:32][N:33]([CH3:47])[C:34]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]1>C1COCC1>[ClH:8].[CH3:32][N:33]([CH3:47])[C:34]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:39][CH2:38][CH:37]([NH:40][C:29](=[O:31])[CH2:28][C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 802Indole-3-Acetic AcidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 69338298HCID 69338298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methylmorpholine (235 μl, 2.1 mmol.) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (371 mg, 2.11 mmol.) were added to a solution of indol-3-ylacetic acid (257 mg) in abs. THF (10 ml). Stirring was then carried out for one hour at RT. The polar diastereomer of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine (320 mg) was then added to the batch, and stirring was carried out for 12 hours at RT. For working up, the mixture was concentrated, the batch was adjusted to pH 11 with 5M NaOH, the phases were separated, and the aqueous phase was diluted with water (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried with Na2SO4 and concentrated. The amide obtained was purified by column chromatography with ethyl acetate/ethanol (1:1) and (120 mg) dissolved in 2-butanone (3 ml) and converted with chlorotrimethylsilane (61 μl) into the corresponding hydrochloride (white solid; 128 mg; 100-102° C.).

Workup

  1. stirringstirring
  2. waitwas carried out for 12 hours at RT
  3. concentrationthe mixture was concentrated
  4. customthe phases were separated
  5. additionthe aqueous phase was diluted with water (10 ml)
  6. extractionextracted with ethyl acetate (3×20 ml)
  7. dry with materialThe combined organic extracts were dried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5f0f7a68e1f440688d73d76dbcec455e
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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