HCID 16718793, compound → HCID 16718835, compound

HRID 1916348Notes

Reaction equation

HRID 1916348 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:32]=[CH:31][C:21]([O:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[C:20]([O:33][CH3:34])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:32]=[CH:31][C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[C:20]([O:33][CH3:34])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 16718793HCID 16718793, compoundHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 16718835HCID 16718835, compoundYield 88%

Procedure

A solution of tert-butyl 2-(4-(6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy)acetate Example 14 (370 mg; 0.741 mmol) in 1:1 TFA/CH2Cl2 (6 mL) was stirred at rt for 1 h. After concentration under reduced pressure and azeotroping with toluene, the residue was triturated with MeOH to afford the title compound (290 mg; 88%) as a white solid. 1H NMR (DMSO-d6) δ 3.79 (s, 3H), 4.75 (s, 2H), 6.99-7.04 (m, 2H), 7.22 (d, J=2.20 Hz, 1H), 7.57 (d, J=8.80 Hz, 2H), 7.91 (d, J=8.25 Hz, 2H), 7.97 (s, 1H), 8.40 (s, 1H), 13.06 (s, 1H); 13C NMR (DMSO-d6) δ 55.76, 64.86, 111.95, 112.70, 119.41, 121.70, 121.98, 127.83, 129.26, 130.21, 131.18, 134.26, 147.36, 148.80, 149.44, 149.79, 156.06, 157.39, 169.9; HPLC (Method #1): 3.44 min retention time; MS (ES): m/z 443 [M+H]+.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customazeotroping with toluene
  3. customthe residue was triturated with MeOH

Sources & evidence

ORD record
ord-13b01ccf1c8348eabfa03f91f4542100
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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