Hydrochloric Acid → HCID 68008386, compound

HRID 75064Notes

Reaction equation

HRID 75064 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[CH2:25][C@H:24]2[CH2:26][C@H:22]([C:23]2([CH3:28])[CH3:27])[C@@H:21]1[NH:29][C:30]1[C:35]([F:36])=[CH:34][N:33]=[C:32]([C:37]2[C:45]3[C:40](=[N:41][CH:42]=[C:43]([Cl:46])[CH:44]=3)[N:39](S(C3C=CC(C)=CC=3)(=O)=O)[CH:38]=2)[N:31]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(#N)C.O1CCOCC1>[Cl:46][C:43]1[CH:44]=[C:45]2[C:37]([C:32]3[N:31]=[C:30]([NH:29][C@@H:21]4[C@@H:20]([CH2:19][OH:18])[CH2:25][C@H:24]5[CH2:26][C@@H:22]4[C:23]5([CH3:27])[CH3:28])[C:35]([F:36])=[CH:34][N:33]=3)=[CH:38][NH:39][C:40]2=[N:41][CH:42]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68008446HCID 68008446, compound2×

Product 1

HCID 68008386HCID 68008386, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-((1R,2S,3S,5R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine, 77f, (0.037 g, 0.046 mmol) in acetonitrile (1.1 mL) was added HCl (0.221 mL of a 4 M solution in dioxane, 0.883 mmol). The mixture was heated to 70° C. for 18 h, during which a precipitate formed. The reaction was concentrated in vacuo and triturated three times with CH3CN to afford 4 mg of the desired product as a white solid: 1H NMR (300.0 MHz, MeOD) δ 8.72-8.64 (m, 1H), 8.39 (s, 1H), 8.32 (d, J=2.3 Hz, 1H), 8.21 (d, J=5.2 Hz, 1H), 4.71 (d, J=6.3 Hz, 1H), 3.67-3.57 (m, 2H), 2.33-2.26 (m, 1H), 2.10 (m, 1H), 1.78-1.70 (m, 1H), 1.28-1.25 (m, 7H) and 1.19 (s, 3H) ppm; LCMS RT=3.13 (M+H) 416.42.

Workup

  1. customformed
  2. concentrationThe reaction was concentrated in vacuo
  3. customtriturated three times with CH3CN

Sources & evidence

ORD record
ord-90c81fca909740bdbd20f133a2f11bb6
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…