Diethylamine → HCID 86601519, compound

HRID 1876245Notes

Reaction equation

HRID 1876245 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=NC#N)[C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2].C(NCC)C>C1COCC1>[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178480854HCID 178480854, compound

Product 1

HCID 86601519HCID 86601519, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Crude 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide (95.0 g; purity 78% HPLC area) in THF (250 mL) was treated with diethylamine (105 g) and refluxed with a concomitant addition of THF (3.35 L) until dissolved. The solvent was distilled off (2.5 L) during which a precipitate was formed. The flask was cooled to ambient temperature and the white precipitate was filtered, washed with ether and dried to give 58.0 g (61% yield) of purified 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol])-2′-ylidenecyanamide (purity >99% HPLC area).

Workup

  1. dissolutionuntil dissolved
  2. distillationThe solvent was distilled off (2.5 L) during which a precipitate
  3. customwas formed
  4. filtrationthe white precipitate was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-ac0ca01e56544d3dad3723387cbca6d1
Source dataset
uspto-grants-2012_11
Patent number
US08309594B2

Reaction notes

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