Water → HCID 86643334, compound

HRID 1948290Notes

Reaction equation

HRID 1948290 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:26]C)=[O:10].B(Br)(Br)Br.C(Cl)Cl.O>C(Cl)Cl.C(#N)C.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[OH:26])=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 22277759Boron tribromide dichloromethaneHCID 86643333HCID 86643333, compound

Product 1

HCID 86643334HCID 86643334, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

Cis(±)2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2 -yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylic acid (Example 35; 100 mg) was suspended in anhydrous DCM. BBr3/DCM (15 ml) was added and the mixture was heated at 40° C. for 18 h. The reaction mixture was cooled to −50° C. and water was added. The mixture was extracted with EtOAc and the organic phase was washed with water, dried over Na2SO4. The organic phase was concentrated in vacuo to yield a pale brown solid which was dissolved in acetonitrile/water mixture and was lyophilized (46 mg). MS (ES) MH+: 419 for C15H16Cl2N4O4S; NMR: 1.87 (m, 2H), 2.20 (s, 3H), 3-4 (brm, 6H), 6.9 (d, 1H), 7.51 (s, 1H), 12.19 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to −50° C.
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationThe organic phase was concentrated in vacuo
  6. customto yield a pale brown solid which

Sources & evidence

ORD record
ord-894145d8b4bb4cb6a2ce0f004acedae4
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…