Hydrochloric Acid → HCID 178518640, compound

HRID 707328Notes

Reaction equation

HRID 707328 reaction equation
C[O:2][C:3]1[N:11]([C@@H:12]2[CH2:15][C@H:14]([NH:16][C:17]3[S:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:13]2)[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=1.Cl>>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[NH:16][C@@H:14]1[CH2:13][C@H:12]([N:11]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[NH:4][C:3]2=[O:2])[CH2:15]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178493982HCID 178493982, compound

Product 1

HCID 178518640HCID 178518640, compoundYield 83%

Procedure

To a 50-mL round-bottomed flask with N-(cis-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)benzo[d]thiazol-2-amine (example 9, 100 mg, 0.285 mmol) was added hydrogen chloride (1 M in diethyl ether, 1.0 mL, 1.0 mmol). The solution was stirred for minutes then concentrated under reduced pressure. The crude was diluted with saturated sodium bicarbonate solution and extracted with dichloromethane (10 mL). The organic extract was dried over sodium sulfate then concentrated in vacuo to give the crude material as a off-white oil. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (4 g, hexane to ethyl acetate gradient) to provide 3-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (40 mg, 0.119 mmol, 83% yield) as light-yellow solid. M+1: 338. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.67-2.80 (m, 2 H) 3.02-3.16 (m, 2 H) 4.12-4.26 (m, 1 H) 4.62-4.77 (m, 1 H) 6.93-7.10 (m, 2 H) 7.22 (td, J=7.20, 1.30 Hz, 1 H) 7.30 (dd, J=7.75, 1.32 Hz, 1 H) 7.37-7.43 (m, 1 H) 7.67 (dd, J=7.75, 0.73 Hz, 1 H) 7.98 (dd, J=5.19, 1.39 Hz, 1 H) 8.50 (d, J=6.72 Hz, 1 H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionThe crude was diluted with saturated sodium bicarbonate solution
  3. extractionextracted with dichloromethane (10 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customto give the crude material as a off-white oil
  8. customThe crude material was absorbed onto a plug of silica gel
  9. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (4 g, hexane to ethyl acetate gradient)

Sources & evidence

ORD record
ord-ae82b6a3fe8a4677a359b1606117a662
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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