Ethanol → HCID 89858026, compound

HRID 1844109Notes

Reaction equation

HRID 1844109 reaction equation
[NH:1]1[CH2:5]C[CH2:3][CH2:2]1.[NH:6]1[CH:10]=[CH:9][CH:8]=[C:7]1/[CH:11]=[C:12]1\[C:13](=[O:35])[NH:14][C:15]2[C:20]\1=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:34])CC(NC1C=CC(F)=CC=1)=O)[CH:16]=2.[NH:36]1C=CC=C1C=O.[CH2:43]([OH:45])C>>[NH:6]1[CH:10]=[CH:9][CH:8]=[C:7]1/[CH:11]=[C:12]1\[C:13](=[O:35])[NH:14][C:15]2[C:20]\1=[CH:19][CH:18]=[C:17]([NH:21][C:22]([N:36]1[CH2:3][CH2:2][N:1]([CH3:5])[C:43]1=[O:45])=[O:34])[CH:16]=2

Participants

5

Reactant 4

HCID 702EthanolHCID 13854Pyrrole-2-carboxaldehydeHCID 31268PyrrolidineHCID 71815105HCID 71815105, compound

Product 1

HCID 89858026HCID 89858026, compound

Procedure

A catalytic amount of pyrrolidine (0.001 mmol) was added to compound D75 (1 mmol) and pyrrole-2-carbaldehyde (1.2 mmol) in ethanol (5 mL). After addition the reaction was carried out using microwave (CEM, Discover) at 100° C. (200 W: Standard mode) for 15 mins. Crude product was precipitated after cooling to RT, collected by filtration, washed with ethanol and air dried. YD: 55.06%; mp: 267-272° C. (charring). 1H NMR (400 MHz, DMSO-d6) δ: 2.788 (s, 3H), 3.420 (t, J=8.2 Hz, 2H), 3.766 (t, J=8.2 Hz, 2H), 6.320 (br, J=3.2 Hz, 1H), 6.767 (br, 1H), 6.879 (dd, J=1.6 & 8.4 Hz, 1H), 7.301 (br, 1H), 7.320 (br, 1H), 7.526 (d, J=8.0 Hz, 1H), 7.599 (s, 1H), 10.480 (s, 1H), 10.872 (s, 1H), 13.198 (s, 1H). (C18H17N5O3) C, H, N.

Workup

  1. additionAfter addition the reaction
  2. customat 100° C.
  3. customfor 15 mins
  4. customCrude product was precipitated
  5. filtrationcollected by filtration
  6. washwashed with ethanol and air
  7. customdried

Sources & evidence

ORD record
ord-d16a07e84be94d5d877be6945ec9a63f
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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