5-Bromo-2-furanecarboxylic acid → HCID 71089659, compound
Reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[NH2:10][CH:11]1[CH:18]2[CH2:19][C:14]3([C:21]([NH2:23])=[O:22])[CH2:15][CH:16]([CH2:20][CH:12]1[CH2:13]3)[CH2:17]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[Br:1][C:2]1[O:6][C:5]([C:7]([NH:10][CH:11]2[CH:12]3[CH2:20][CH:16]4[CH2:15][C:14]([C:21](=[O:22])[NH2:23])([CH2:19][CH:18]2[CH2:17]4)[CH2:13]3)=[O:9])=[CH:4][CH:3]=1Participants
5
Procedure
To a solution prepared by dissolving 100 mg of 5-bromofuran-2-carboxylic acid, 145 mg of (E) type 4-aminoadamantane-1-carboxylic acid amide (prepared from Preparation Example 1), and 202 mg of TBTU in MC was added dropwise 0.2 mL of DIEA and then stirred at room temperature for 4 hours. The reaction solution was washed with a 1N solution of HCl and a 1N solution of NaOH, respectively, and then washed again with brine. The resulting organic solution was dried over MgSO4 and after filtration, was distilled under a reduced pressure. The compound thus obtained was purified via recrystallization by using MeOH and ether to produce 150 mg of a white solid product.
Workup
- customTo a solution prepared
- washThe reaction solution was washed with a 1N solution of HCl
- washa 1N solution of NaOH, respectively, and then washed again with brine
- dry with materialThe resulting organic solution was dried over MgSO4
- filtrationafter filtration
- distillationwas distilled under a reduced pressure
- customThe compound thus obtained
- customwas purified via recrystallization
Sources & evidence
- ORD record
- ord-cbf02cc563084a3c844e97a8e7f0ef88
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233957B2
Reaction notes
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