Ammonium Chloride → HCID 68008446, compound

HRID 75063Notes

Reaction equation

HRID 75063 reaction equation
[Si:1]([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])[CH:21]1[NH2:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:30][C:31]1[CH:32]=[C:33]2[C:39]([C:40]3[N:45]=[C:44](S(C)=O)[C:43]([F:49])=[CH:42][N:41]=3)=[CH:38][N:37]([S:50]([C:53]3[CH:59]=[CH:58][C:56]([CH3:57])=[CH:55][CH:54]=3)(=[O:52])=[O:51])[C:34]2=[N:35][CH:36]=1.C(N(C(C)C)CC)(C)C.[NH4+].[Cl-]>CN(C=O)C>[Si:1]([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:42]1[C:43]([F:49])=[CH:44][N:45]=[C:40]([C:39]2[C:33]3[C:34](=[N:35][CH:36]=[C:31]([Cl:30])[CH:32]=3)[N:37]([S:50]([C:53]3[CH:59]=[CH:58][C:56]([CH3:57])=[CH:55][CH:54]=3)(=[O:52])=[O:51])[CH:38]=2)[N:41]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridineHCID 68008164(1R,3S,5R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-6,6-dimethyl-bicyclo[3.1.1]heptan-2-amine2×

Product 1

HCID 68008446HCID 68008446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (1R,3S,5R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-6,6-dimethyl-bicyclo[3.1.1]heptan-2-amine, 77e, (0.20 g, 0.46 mmol) and 5-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.14 g, 0.30 mmol) in DMF (1.5 mL) was added diisopropylethylamine (0.11 mL, 0.61 mmol). The reaction was heated to 75° C. for 18 hours. The mixture was diluted into aqueous saturated NH4Cl solution and extracted twice with EtOAc. The combined organic phases were washed twice with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (0-5% MeOH/CH2Cl2 gradient) to afford 78 mg of the desired product.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed twice with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified via silica gel chromatography (0-5% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-84ec44cc09bf4213b17895e5ebffad13
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…