Water → HCID 86636090, compound

HRID 641710Notes

Reaction equation

HRID 641710 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:25])[CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([CH:23]=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.O.CN([CH:35]=[O:36])C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([C:23]([CH:35]=[O:36])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:25])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 58399171HCID 58399171, compound

Product 1

HCID 86636090HCID 86636090, compound

Procedure

To a solution of the product from Step 9 of Example 1 (15 mg) in 2 mL of DMF was added 15 μL of POCl3. After stirring for 10 min, 2 mL of water was added and the reaction mixture was stirred for 24 h. The solid was collected by filtration to give the title compound (˜16 mg). 1H NMR (500 MHz, acetone-d6) δ 10.11 (s, 1H), 8.15 (m, 1H), 8.10 (m, 2H), 7.48 (t, 2H), 7.45 (m, 1H), 7.27 (m, 2H), 4.68 (m, 1H), 4.30 (m, 1H), 4.06 (t, 1H), 3.62-3.68 (m, 1H), 3.18-3.27 (m, 1H), 3.10 (s, 3H), 2.10 (m, 1H), 1.78 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred for 24 h
  2. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-f7591560009d4bc98e886f54d4be2aa5
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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