Hydrochloric Acid → HCID 118036533, compound

HRID 1778088Notes

Reaction equation

HRID 1778088 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[N:18][C:19]=1[CH:20](OC)[O:21]C)[N:16]([C:25]([NH:27][C:28]1[CH:33]=[C:32]([NH:34][C@H:35]3[C@@H:40]([CH2:41][O:42][Si](CC)(CC)CC)[C@H:39]4[CH2:50][C@@H:36]3[CH2:37][CH2:38]4)[C:31]([C:51]#[N:52])=[CH:30][N:29]=1)=[O:26])[CH2:15][CH2:14][CH2:13]2)(C(C)(C)C)(C)C.O.Cl>C1COCC1>[C:51]([C:31]1[C:32]([NH:34][C@H:35]2[C@@H:40]([CH2:41][OH:42])[C@H:39]3[CH2:50][C@@H:36]2[CH2:37][CH2:38]3)=[CH:33][C:28]([NH:27][C:25]([N:16]2[C:17]3[C:12](=[CH:11][C:10]([CH2:9][OH:8])=[C:19]([CH:20]=[O:21])[N:18]=3)[CH2:13][CH2:14][CH2:15]2)=[O:26])=[N:29][CH:30]=1)#[N:52]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131734799HCID 131734799, compound

Product 1

HCID 118036533HCID 118036533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Racemic 6-(((tert-butyldimethylsilyl)oxy)methyl)-N-(5-cyano-4-(((1S*,2R*,3S*,4R*)-3-(((triethylsilyl)oxy)methyl)bicyclo[2.2.1]heptan-2-yl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 37N, 64 mg, 0.085 mmol) was dissolved in THF (2 ml) and water (1 ml) and treated with conc. HCl (0.28 ml). The reaction mixture was stirred 30 h at room temperature. The reaction mixture was then quenched with sat. aq. NaHCO3 and extracted 3× with DCM. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The residue was triturated in a small quantity of DCM and then, the product was precipitated by addition of heptanes. The solid was collected by centrifugation and dried to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was then quenched with sat. aq. NaHCO3
  2. extractionextracted 3× with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated in a small quantity of DCM
  7. customthe product was precipitated by addition of heptanes
  8. customThe solid was collected by centrifugation
  9. customdried

Sources & evidence

ORD record
ord-275c41982a5a4b3d8070e08887e7ba55
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…