Dimethylformamide → HCID 10893859, compound

HRID 724530Notes

Reaction equation

HRID 724530 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].CN(C=O)C.C(N(C(C)C)CC)(C)C.[NH2:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35]([C:40]([OH:42])=[O:41])=[CH:34]2>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([NH:30][C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][C:35]([C:40]([OH:42])=[O:41])=[CH:34]4)=[O:14])=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 14771285-Nitrobenzofuran-2-carboxylic acidHCID 153403775-Amino-1H-indole-2-carboxylic acid

Product 1

HCID 10893859HCID 10893859, compound

Procedure

To the solution of 93.2 mg (0.45 mmol) 5-nitrobenzofuran-2-carboxylic acid (128) in 6 mL DMF 209.0 mg (0.45 mmol) PyBroP and 157 μL (0.9 mmol) diisopropylethylamine was added and the clear solution was stirred for 10 minutes at room temperature. The activated acid was transferred to resin 127 which was agitated for 5 hrs. The resin was drained, washed twice with DMF. The analytical sample showed no complete reaction and therefore the activation/coupling reaction was repeated once again the same way using fresh reagents. The resin was drained, washed five times with DMF to give 129 which was used immediately as described in Example 117.

Workup

  1. stirringwas agitated for 5 hrs
  2. washwashed twice with DMF
  3. customno complete reaction
  4. customthe activation/coupling reaction
  5. washwashed five times with DMF

Sources & evidence

ORD record
ord-6d87b4251a8346baa30bfa1c11509a94
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

Loading…