Water → HCID 67062570, compound

HRID 598854Notes

Reaction equation

HRID 598854 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:15]=[C:14]([NH:16][C:17](=[O:22])[O:18][CH2:19][CH:20]=[CH2:21])[O:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([N@:35]2[CH2:37][CH:36]2[CH2:38][C:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[NH:41][CH:40]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([O-:25])=[O:24].O>CN(C=O)C>[NH:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39]([CH2:38][C@H:36]([NH:35][S:32]([C:29]2[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:31][CH:30]=2)(=[O:33])=[O:34])[CH2:37][N:16]([C:14]2[O:13][N:12]=[C:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[CH:1]=[N:2][CH:3]=[CH:4]4)[CH:15]=2)[C:17](=[O:22])[O:18][CH2:19][CH:20]=[CH2:21])=[CH:40]1

Participants

5

Reactant 3

HCID 962WaterHCID 57950560Allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamateHCID 178526728HCID 178526728, compound

Product 1

HCID 67062570HCID 67062570, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 25 mL of round-bottom flask was added allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate (68 mg, 230 μmol) (prepared as shown for Example 11), 1,8-diazabicyclo(5.4.0)-7-undecene (6.8 μl, 46 μmol) and 2 mL of DMF at room temperature. (S)-3-((1-(4-Nitrophenylsulfonyl)aziridin-2-yl)methyl)-1H-indole (98 mg, 276 μmol) (prepared as described in US Patent Publication No. US 2007/0173506 which is hereby incorporated by reference in its entirety and for all purposes as if specifically set forth herein) in 1 mL of DMF was added to the reaction mixture dropwise. After 3 hours, 10 mL of water was added, and then the reaction mixture was extracted twice with 20 mL of EtOAc. The extracts were combined, concentrated under reduced pressure, and purified by flash chromatography on silica gel (65% EtOAc/hexane) to give allyl(S)-3-(1H-indol-3-yl)-2-(4-nitrophenylsulfonamido)propyl(3-(isoquinolin-6-yl)isoxazol-5-yl)carbamate (130 mg, 86% yield). MS m/z: 653 (M+1).

Workup

  1. additionwas added to the reaction mixture dropwise
  2. extractionthe reaction mixture was extracted twice with 20 mL of EtOAc
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography on silica gel (65% EtOAc/hexane)

Sources & evidence

ORD record
ord-811ae2b58aba49fa9dae4396f902f33d
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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