Sodium Hydroxide → HCID 66752569, compound

HRID 1785415Notes

Reaction equation

HRID 1785415 reaction equation
[CH3:1][N:2]([CH3:43])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]2[N:16]=[C:15]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:14]3=[CH:13][C:12]=2[C:11](=[O:23])[N:10]([CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28](C(NCCN(C)C)=O)[CH:27]=2)[CH:9]=1)=[O:7].[OH-].[Na+]>C(O)C>[CH3:43][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:17]2[N:16]=[C:15]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:14]3=[CH:13][C:12]=2[C:11](=[O:23])[N:10]([CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][CH:27]=2)[CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66752565HCID 66752565, compound

Product 1

HCID 66752569HCID 66752569, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a hot solution of the bisamide 21b (0.58 g, 1.00 mmol) in ethanol (10 mL) was added 10% sodium hydroxide (10 mL), and the whole was heated at reflux for 40 min. The reaction mixture was then evaporated to dryness under reduced pressure, water was added and the solid was filtered and washed with water to give 20v as a gold solid (0.42 g, 90%), mp 105-107° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.31 [s, 6H, N(CH3)2], 2.64 (t, J=6.4 Hz, 2H, CH2CH2NMe2), 2.82 (s, 3H, ArCH3), 3.21 (t, J=7.7 Hz, 2H, CH2CH2Indole), 3.73 (q, J=6.1 Hz, 2H, CH2CH2NMe2), 4.30 (t, J=7.8 Hz, 2H, CH2CH2Indole), 6.99 (d, J=2.0 Hz, 1H, H-2′), 7.06-7.14 (m, 2H, H-5′, H-6′), 7.30 (d, J=7.7 Hz, 1H, H-7′), 7.46 (t, J=7.6 Hz, 1H, H-8), 7.66-7.70 (m, 2H, H-4′, H-7), 7.82 (d, J=8.2 Hz, 1H, H-9), 8.51 (s, 1H, H-3), 8.62 (s, 1H, H-1′), 9.24 (s, 1H, H-10), 10.98 (br t, J=5.3 Hz, 1H, CONH). 13C NMR (CDCl3): δ 18.2 (ArCH3), 24.8 (CH2CH2Indole), 37.2 (CH2CH2NMe2), 45.0 [N(CH3)2], 50.2 (CH2CH2Indole), 58.4 (CH2CH2NMe2), 109.0 (C), 110.9 (CH, C-7′), 111.1 (C), 118.2 (CH, C-4′), 119.2 (CH, C-5′), 121.7 (CH, C-6′), 122.0 (CH, C-2′), 125.6 (C-9a), 126.2 (CH, C-8), 126.8 (C-3a′), 127.0 (CH, C-9), 132.5 (CH, C-7), 135.5 (C-6), 136.0 (C-7a′), 139.5 (CH, C-3), 142.7 (CH, C-10), 147.8 (C-5a), 148.4 (C-4a), 162.1 (C-1), 164.4 (CONH). Indole C-3′ was not observed.

Workup

  1. temperaturethe whole was heated
  2. temperatureat reflux for 40 min
  3. customThe reaction mixture was then evaporated to dryness under reduced pressure, water
  4. additionwas added
  5. filtrationthe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-2680ae286fb04a19bde451735abd188d
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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