Water → HCID 58126905, compound

HRID 1971849Notes

Reaction equation

HRID 1971849 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20]([N:22]3[CH2:27][C@@H:26]([CH3:28])[O:25][C@@H:24]([CH3:29])[CH2:23]3)=[O:21])[C:12]2=[N:11][C:10]=1[C:30]1[S:31][C:32]([CH2:35][C:36]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:37]=2[C:38]([NH2:40])=O)=[CH:33][N:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CN(C=O)C.O=P(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][N:18]([CH2:19][C:20]([N:22]3[CH2:27][C@@H:26]([CH3:28])[O:25][C@@H:24]([CH3:29])[CH2:23]3)=[O:21])[C:12]2=[N:11][C:10]=1[C:30]1[S:31][C:32]([CH2:35][C:36]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:37]=2[C:38]#[N:40])=[CH:33][N:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 58127013HCID 58127013, compound

Product 1

HCID 58126905HCID 58126905, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of the product of example 117 (15 mg, 0.024 mmol) in DMF (0.5 ml), POCl3 (0.1 ml) was added drop-wise. The mixture was stirred at room temperature for 20 hours, after which water was added, and then extracted with CH2Cl2. The extracts were combined, washed with brine, and then dried over sodium sulfate. The product was purified by column chromatography (CH2Cl2/EA/MeOH=8/2/1) to give the desired product (6 mg, 40% yield).

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe product was purified by column chromatography (CH2Cl2/EA/MeOH=8/2/1)

Sources & evidence

ORD record
ord-68e8700693b74150b7f8e16bae43be84
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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