Tetrahydrofuran → HCID 178515079, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([NH:11][C:12]([CH3:15])(C)C)[C:8]([O-:10])=O.N1C=CC=C1C(NC1[CH:33](C(O)=O)[C:32](=[O:37])[C:31]2[C:26](=[CH:27][C:28]([Cl:38])=[CH:29][CH:30]=2)[N:25]=1)=O.C(N=C=NC(C)C)(C)C.[O:48]1CCCC1>>[Cl:38][C:28]1[CH:29]=[CH:30][C:31]2[C:32](=[O:37])[C:33]3[C:8](=[O:10])[N:7]([CH2:6][C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[N:11]=[C:12]([OH:48])[C:15]=3[NH:25][C:26]=2[CH:27]=1Participants
Procedure
To a solution of 2-(thiophen-2-ylmethyl)-t-butylcarbazate (1.0 g, 4.4 mM) and 2-pyrrolamido-3-carboxy-7-chloroquinoline-4-one (1.2 g, 3.6 mM) in tetrahydrofuran (75 mL) stirred at room temperature, was added diisopropylcarbodiimide (0.84 mL, 5.4 mM). This mixture was stirred at room temperature for 2.5 hours, then suction filtered into a second reaction flask. To the filtrate (stirred at room temperature) was added methanesulfonic acid (12 mL, 185 mM). The resulting solution was stirred 17 hours at room temperature. TLC analyses at this time indicated complete reaction. The reaction mixture was poured into ice water (200 mL). This suspension was stirred about 15 minutes and filtered. The filter cake was washed with water and ether, then vacuum dried to yield the desired compound analytically pure (1.1 g, 84%).
Workup
- filtrationsuction filtered into a second reaction flask
- stirringTo the filtrate (stirred at room temperature)
- additionwas added methanesulfonic acid (12 mL, 185 mM)
- stirringThe resulting solution was stirred 17 hours at room temperature
- customreaction
- stirringThis suspension was stirred about 15 minutes
- filtrationfiltered
- washThe filter cake was washed with water and ether
- customvacuum dried
Sources & evidence
- ORD record
- ord-aee4adfbcd9649f2addaa22cee5cb884
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06214826B1
Reaction notes
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