Dimethylformamide → HCID 118235501, compound

HRID 626990Notes

Reaction equation

HRID 626990 reaction equation
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][C:23]([N:26]4[CH2:31][CH2:30][C:29]([CH3:35])([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]4)=[N:24][CH:25]=3)[CH:18]=[CH:19][C:14]2=[N:13][C:12]=1[CH3:36].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[N:49]1([CH2:55][CH2:56]O)[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>ClCCl>[F:37][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][C:23]([N:26]4[CH2:31][CH2:30][C:29]([CH3:35])([C:32]([O:34][CH2:56][CH2:55][N:49]5[CH2:54][CH2:53][O:52][CH2:51][CH2:50]5)=[O:33])[CH2:28][CH2:27]4)=[N:24][CH:25]=3)[CH:18]=[CH:19][C:14]2=[N:13][C:12]=1[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 611632-MorpholinoethanolHCID 65578Oxalyl chlorideHCID 72722114HCID 72722114, compound

Product 1

HCID 118235501HCID 118235501, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The sodium salt of Example 44 (200 mg, 0.378 mmol) was suspended in dichloromethane (25 mL). A drop of DMF was added, followed by oxalyl chloride (50 mg, 0.39 mmol). The mixture was stirred at room temperature for 2 h, then 2-(morpholin-4-yl)ethanol (99 mg, 0.75 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed with aqueous sodium bicarbonate solution and the organic layer was concentrated in vacuo. Chromatography (silica, 0 to 10% MeOH in DCM), followed by freeze-drying, gave the title compound (35 mg, 15%) as an off-white solid. δH (DMSO-d6) 8.64 (s, 2H), 8.37 (s, 1H), 7.55-7.43 (m, 2H), 7.31-7.10 (m, 4H), 7.04-7.01 (m, 1H), 4.35 (s, 2H), 4.34-4.28 (m, 2H), 4.25-4.21 (m, 2H), 3.52-3.48 (m, 4H), 3.36-3.25 (m, 2H), 2.60-2.54 (m, 2H), 2.42-2.38 (m, 4H), 2.32 (s, 3H), 2.10-2.04 (m, 2H), 1.45-1.35 (m, 2H), 1.19 (s, 3H). LCMS (pH10): MH+ (621.8), RT 2.01 minutes.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate solution
  3. concentrationthe organic layer was concentrated in vacuo
  4. customby freeze-drying

Sources & evidence

ORD record
ord-9e220e0ee7394b03b23545f4aa158ccd
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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