Hydrochloric Acid → HCID 58074319, compound

HRID 1174555Notes

Reaction equation

HRID 1174555 reaction equation
N(C(C)C)C(C)C.[Li]CCCC.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([N:22]1[C:28]2[CH:29]=[CH:30][S:31][C:27]=2[C:26](=[O:32])[NH:25][CH2:24][CH2:23]1)[CH3:21].C(O[B:37]1[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]1)(C)C.Cl>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([N:22]1[C:28]2[CH:29]=[C:30]([B:37]3[O:41][C:40]([CH3:43])([CH3:42])[C:39]([CH3:45])([CH3:44])[O:38]3)[S:31][C:27]=2[C:26](=[O:32])[NH:25][CH2:24][CH2:23]1)[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58074318HCID 58074318, compoundHCID 178418339Butyllithium

Product 1

HCID 58074319HCID 58074319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

HNiPr2 (246 μL, 1.74 mmol, 3.0 Eq) was dissolved in anhydrous THF (10 mL) and cooled to −78° C. under nitrogen. 2.5 M BuLi in hexanes (700 μL, 1.74 mmol, 3.0 Eq) was added dropwise and the reaction stirred at −78° C. for 15 minutes then warmed to 0° C. for 30 minutes. The reaction was cooled to −78° C. and 1-[1-(2-chloro-phenyl)-ethyl]-1,2,3,4-tetrahydro-thieno[3,2-e][1,4]diazepin-5-one (178 mg, 0.58 mmol, 1.0 Eq) was in anhydrous THF (5 mL) was added dropwise. The reaction was stirred at −78° C. for 2 hours. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (355 μL, 1.74 mmol, 3.0 Eq) in anhydrous THF (5 mL) was added and the reaction stirred at −78° C. for 20 minutes them warmed to ambient temperature for 1.5 hours. 1M HCl (20 mL) was added and the mixture extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine (40 mL), dried (MgSO4) and concentrated in vacuo. The yellow oil obtained was used without further purification; 1H NMR (DMSO D6) 1.28 (12H, s), 1.51 (3H, d), 2.93-2.99 (1H, m), 3.03-3.13 (2H, m), 3.20-3.26 (1H, m), 5.32 (1H, dd), 6.19 (1H, br s), 7.20-7.28 (3H, m), 7.33-7.36 (2H, m); LC/MS M+1 (obs.) 433.4.

Workup

  1. temperaturethen warmed to 0° C. for 30 minutes
  2. temperatureThe reaction was cooled to −78° C.
  3. additionwas added dropwise
  4. stirringThe reaction was stirred at −78° C. for 2 hours
  5. stirringthe reaction stirred at −78° C. for 20 minutes them
  6. temperaturewarmed to ambient temperature for 1.5 hours
  7. extractionthe mixture extracted with EtOAc (3×40 mL)
  8. washThe combined organic extracts were washed with brine (40 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe yellow oil obtained
  12. customwas used without further purification

Sources & evidence

ORD record
ord-ce71456d713e4f459145061018a0afcb
Source dataset
uspto-grants-2010_11
Patent number
US07838517B2

Reaction notes

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