Acetyl chloride → HCID 73775523, compound

HRID 712105Notes

Reaction equation

HRID 712105 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[NH2:8][CH:9]([C:11]1[N:22]([C@@H:23]2[CH2:28][O:27][C@@H:26]([CH2:29][C:30]#[N:31])[CH2:25][CH2:24]2)[C:14]2=[C:15]3[S:21][CH:20]=[CH:19][C:16]3=[N:17][CH:18]=[C:13]2[N:12]=1)[CH3:10].C(N(CC)CC)C.C(Cl)(=O)C>C(Cl)Cl>[C:30]([CH2:29][C@@H:26]1[O:27][CH2:28][C@@H:23]([N:22]2[C:14]3=[C:15]4[S:21][CH:20]=[CH:19][C:16]4=[N:17][CH:18]=[C:13]3[N:12]=[C:11]2[CH:9]([NH:8][C:3](=[O:5])[CH3:2])[CH3:10])[CH2:24][CH2:25]1)#[N:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86717558HCID 86717558, compound

Product 1

HCID 73775523HCID 73775523, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of {(2R,5S)-5-[2-(1-aminoethyl)-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl]tetrahydro-2H-pyran-2-yl}acetonitrile trifluoroacetate (8.0 mg, 0.018 mmol) (Example 68) and triethylamine (12 μL, 0.088 mmol) in methylene chloride (0.15 mL) was added acetyl chloride (2.0 μL, 0.028 mmol). The resulting mixture was stirred at room temperature for 3 h and then concentrated. The residue was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give 3.5 mg (52%) of the desired product. LCMS calculated for C19H22N5O2S (M+H)+: m/z=384.1. Found: 384.2.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-b442c5852b3f42f0a5fdbbac3266660f
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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