Sodium Hydroxide → HCID 67550255, compound

HRID 1829967Notes

Reaction equation

HRID 1829967 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:35])[CH:7]=[C:8]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22](=[O:34])[NH:23][C:24]2[CH:28]=[C:27]([C:29]([O:31]C)=[O:30])[N:26]([CH3:33])[CH:25]=2)=[CH:16]3)=[O:12])[CH:9]=1)=[O:4].[OH-].[Na+]>O.CO>[OH:31][C:29]([C:27]1[N:26]([CH3:33])[CH:25]=[C:24]([NH:23][C:22]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([C:11]([NH:10][C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:35])[CH:7]=2)=[O:12])=[CH:21][CH:20]=3)=[O:34])[CH:28]=1)=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 675501654-({1-[2-(5-methoxycarbonyl-1 methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2carboxylic acid methyl ester

Product 1

HCID 67550255HCID 67550255, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-({1-[2-(5-methoxycarbonyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2carboxylic acid methyl ester 8 (1.04 g, 2.18 mmole) and NaOH (10 mmole) in a mixture of water/MeOH (1/4) (25 ml) was stirred at 50° C. for 6 h and then overnight at ambient temperature. The reaction mixture was evaporated in vacuo to dryness and the residue was dissolved in water (50 ml) and acidified with 1M HCl up to pH=3. The precipitate was collected on the filter and washed with water (3×50 ml) and dried over phosphorus pentoxide in dessicator to give 0.85 g (87%) of 4-({1-[2-(5-hydroxycarbonyl-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid 9 as white crystalline material. MS: 448.08 (M−H). 1H-NMR (DMSO-d6): δ 11.96 (s, 1H, H-1, indole); 10.45,10.25 (s,s, 1H,1H, —C(═O)NH); 8.30 (m, 1H, H-6, indole); 7.48 (m, 3H, H-7, indole); 7.49,7.46 (d,d, H-3 or H-5, Py1,Py2); 7.39 (s, 1H, H-3, indole); 6.91 (m, 2H, H-3 or H-5, Py1,Py2); 3.84,3.83 (s,s, 6H, NCH3, Py1,Py2).

Workup

  1. customovernight
  2. customat ambient temperature
  3. customThe reaction mixture was evaporated in vacuo to dryness
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. customThe precipitate was collected on the
  6. filtrationfilter
  7. washwashed with water (3×50 ml)
  8. dry with materialdried over phosphorus pentoxide in dessicator

Sources & evidence

ORD record
ord-d1f7ffceea3045ff8d1d2cf4e7b704ee
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Reaction notes

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