Water → 4-(2-(Benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoic acid

HRID 1772725Notes

Reaction equation

HRID 1772725 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]#[C:11][C:12]1[N:13]=[C:14]2[C:19]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:18][CH:17]=[C:16]([C:26]3[CH:38]=[CH:37][C:29]([C:30]([O:32]C(C)(C)C)=[O:31])=[CH:28][CH:27]=3)[N:15]2[CH:39]=1.C(O)(C(F)(F)F)=O.O>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]#[C:11][C:12]1[N:13]=[C:14]2[C:19]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:18][CH:17]=[C:16]([C:26]3[CH:38]=[CH:37][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)[N:15]2[CH:39]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 117732304tert-Butyl 4-(2-(benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

Product 1

HCID 863458984-(2-(Benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 81c (49 mg, 0.09 mmol) in dichloromethane (4 mL), TFA (1 mL, 13 mmol) was added. The mixture was stirred at rt for 18 h and concentrated under reduced pressure. The oil obtained was dissolved in dichloromethane and water was added. The resultant precipitate was collected by filtration to afford the title compound 11. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 13.18 (s, 1H), 8.60 (s, 1H), 8.20 (d, J=8.2 Hz, 1H), 8.13-8.11 (m, 3H), 7.85 (d, J=8.3 Hz, 2H), 7.66-7.57 (m, 3H), 4.29 (m, 4H), 3.82 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C26H20N5O3S: (M+H) 482.1. Found 482.4.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe oil obtained
  3. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-88df8f94d3314283bed37f15a73853f7
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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