Hydrochloric Acid → HCID 57527216, compound
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C@H:11]([NH:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([CH2:25][C:26]#[N:27])[CH:22]=[CH:21][C:19]=2[N:20]=1)([CH2:13][CH3:14])[CH3:12].[F:28][C:29]1[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=1[C:31](OC)=[O:32].Cl>C1COCC1>[C@H:11]([NH:15][C:16]1[S:17][C:18]2[CH:24]=[C:23]([CH:25]([C:31]([C:30]3[CH:35]=[CH:36][CH:37]=[CH:38][C:29]=3[F:28])=[O:32])[C:26]#[N:27])[CH:22]=[CH:21][C:19]=2[N:20]=1)([CH2:13][CH3:14])[CH3:12]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 35.3 mL) in THF (60 mL) was added a solution of (R)-2-(2-(sec-butylamino)benzo[d]thiazol-6-yl)acetonitrile (3.74 g, 15.2 mmol) in THF (60 mL) at −78° C. over 40 min. The resulting solution was stirred at −78° C. for 10 min before a solution of methyl 2-fluorobenzoate (2.5 mL, 19.6 mmol) in THF (15 mL) was added over 5 min. The mixture was stirred at −78° C. for 1 hr and then at rt for 3 hr before it was poured into ice-cold water (100 mL). After its pH value was adjusted to 9 with 6 N HCl, the mixture was extracted with AcOEt (3×60 mL). The combined extract was washed with brine and dried over anhydrous MgSO4. The solution was concentrated under vacuum, and the residue was subjected to ISCO (2% MeOH/CH2Cl2) to give a mixture (4.09 g) of the title compound and the starting material in a ratio of 1:1.
Workup
- additionwas added over 5 min
- extractionthe mixture was extracted with AcOEt (3×60 mL)
- extractionThe combined extract
- washwas washed with brine
- dry with materialdried over anhydrous MgSO4
- concentrationThe solution was concentrated under vacuum
Sources & evidence
- ORD record
- ord-0853584a826b42c5b8ce2130273bdb90
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473784B2
Reaction notes
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