Dimethylformamide → HCID 178527291, compound

HRID 1429394Notes

Reaction equation

HRID 1429394 reaction equation
O=[C:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:3][NH:4][C:5](=O)[CH2:6][C@H:7]1[N:14]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)(=[O:17])=[O:16])[CH2:13][C:12]2[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=2[CH2:10][O:9][CH2:8]1.C([O-])(C)=O.[NH4+].C[N:45](C=O)C>O>[C:33]1([C:2]2[N:45]=[C:5]([CH2:6][C@H:7]3[N:14]([S:15]([C:18]4[CH:19]=[CH:20][CH:21]=[C:22]5[C:27]=4[N:26]=[CH:25][CH:24]=[CH:23]5)(=[O:16])=[O:17])[CH2:13][C:12]4[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=4[CH2:10][O:9][CH2:8]3)[NH:4][CH:3]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 71269526HCID 71269526, compound

Product 1

HCID 178527291HCID 178527291, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A microwave tube was charged with compound 28a (100 mg, 0.19 mmol), AcONH4 (44 mg, 0.57 mmol) and DMF (3 mL), and then was sealed and heated to 150° C. for 1 h under microwave irradiation. The mixture was taken up in H2O (10 mL) and extracted with DCM (30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by Prep-TLC to give compound 28 (30 mg, 30% yield). LCMS (m/z): 511.1 (MH+).

Workup

  1. customwas sealed
  2. extractionextracted with DCM (30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by Prep-TLC

Sources & evidence

ORD record
ord-75eb2cafcd4a4e318605273a788056f8
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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