Methanol → HCID 131714807, compound

HRID 364169Notes

Reaction equation

HRID 364169 reaction equation
C(N(CC)CC[N:6]1[C:14]2[CH:13]=[CH:12][C:11](NC(=O)CN(CCOCC3C=CC=CC=3)CC3C=CC=CC=3)=[C:10]3[O:37][C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][C:39]=4[C:8]([C:9]=23)=[N:7]1)C.CO>O1CCCC1>[N:7]1[NH:6][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[O:37][C:38]4[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][C:39]=4[C:8]=1[C:9]=23

Participants

4

Reactant 2

HCID 887MethanolHCID 13689017HCID 13689017, compound

Product 1

HCID 131714807HCID 131714807, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2.45 g of N-[2-[2-(diethylamino)-ethyl]-9-hydroxy-2H-[1]benzopyrano[4,3,2-cd]indazol-5-yl]-2-[[2-(phenylmethoxy)ethyl](phenylmethyl)amino]acetamide in 80 ml of dry tetrahydrofuran under argon was added 40 ml of 1M solution of borane tetrahydrofuran complex in tetrahydrofuran. After 24 hours at 50° C., an additional 3 ml of borane tetrahydrofuran complex was added and the reaction continued for another three hours at 50° C. The mixture was poured into 150 ml of methanol, heated under reflux overnight, evaporated to dryness, and the residue of crystallized from diethyl ether to afford 1.36 g of 2-[2-diethylamino)ethyl]-5-[[2-(phenylmethoxy)ethyl](phenylmethyl)amino]ethyl]amino]-2H-[1]benzopyrano[4,3,2-cd]indazol-9-ol.

Workup

  1. additionan additional 3 ml of borane tetrahydrofuran complex was added
  2. waitthe reaction continued for another three hours at 50° C
  3. temperatureheated
  4. temperatureunder reflux overnight
  5. customevaporated to dryness
  6. customthe residue of crystallized from diethyl ether

Sources & evidence

ORD record
ord-eeaf3aff35a64dfc8897c604e49c0fd1
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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