Butyronitrile → HCID 73775526, compound

HRID 712094Notes

Reaction equation

HRID 712094 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C@H:4]([N:7]2[C:11]3=[C:12]4[S:18][CH:17]=[CH:16][C:13]4=[N:14][CH:15]=[C:10]3[N:9]=[C:8]2[C@H:19]([OH:21])[CH3:20])[CH2:3]1.C(N(CC)C(C)C)(C)C.[C:31](#[N:35])[CH2:32][CH2:33][CH3:34]>C(#N)C>[OH:21][C@@H:19]([C:8]1[N:7]([C@H:4]2[CH2:5][CH2:6][N:2]([CH2:34][CH2:33][CH2:32][C:31]#[N:35])[CH2:3]2)[C:11]2=[C:12]3[S:18][CH:17]=[CH:16][C:13]3=[N:14][CH:15]=[C:10]2[N:9]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8008ButyronitrileHCID 81531DiisopropylethylamineHCID 86717547HCID 86717547, compound

Product 1

HCID 73775526HCID 73775526, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (1R)-1-{1-[(3S)-pyrrolidin-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol hydrochloride (15 mg, 0.046 mmol) and N,N-diisopropylethylamine (24 μL, 0.14 mmol) in acetonitrile (0.2 mL) was added butanenitrile, 4-bromo- (5.1 μL, 0.051 mmol). The resulting mixture was stirred at rt for 4 h. The mixture was diluted and 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 6.3 mg (38%) of the desired product. LCMS calculated for C18H22N5OS (M+H)+: m/z=356.2. Found: 356.0.

Workup

  1. additionThe mixture was diluted
  2. custompurified
  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-f7350487cf8947d49ab7157ea1cb7efc
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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