Hydrochloric Acid → HCID 118036692, compound

HRID 1777892Notes

Reaction equation

HRID 1777892 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]([N:34]3[CH2:50][CH2:49][C:37]4([CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]4)[CH2:36][CH2:35]3)[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.Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[C:51]([C:31]1[C:32]([N:34]2[CH2:35][CH2:36][C:37]3([CH2:41][NH:40][CH2:39][CH2:38]3)[CH2:49][CH2:50]2)=[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

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 131734778HCID 131734778, compound2×

Product 1

HCID 118036692HCID 118036692, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 8-(2-(6-(((tert-butyldimethylsilyl)oxy)methyl)-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine-1-carboxamido)-5-cyanopyridin-4-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate (intermediate 37D, 70 mg, 0.095 mmol) in THF (0.5 ml) and H2O (0.5 ml) was added conc. HCl (0.1 ml, 1.2 mmol). The reaction mixture was stirred at room temperature for 4 h, then conc. HCl (0.1 ml, 1.2 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into sat. aq. NaHCO3 and extracted with DCM (4×) and EtOAc (4×). The combined organic phases were then dried over Na2SO4, filtered and evaporated. The crude material was triturated with EtOAc and dried under high vacuum to give the title compound as an off-white powder. (UPLC-MS 3) tR 0.64 min; ESI-MS 476.2 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with DCM (4×) and EtOAc (4×)
  3. dry with materialThe combined organic phases were then dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was triturated with EtOAc
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-e67da93245f44965b2b052794277f7e1
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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