Triethylamine → HCID 178462245, compound

HRID 712136Notes

Reaction equation

HRID 712136 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH2:15][CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[C:27]3=[C:28]4[S:34][CH:33]=[CH:32][C:29]4=[N:30][CH:31]=[C:26]3[N:25]=[C:24]2[C@H:35]([OH:37])[CH3:36])[CH2:19][CH2:18]1.C(N(CC)CC)C.[C:45](=O)([O:56][CH:57]1[CH2:61][CH2:60][O:59][CH2:58]1)[O:46]C1C=CC([N+]([O-])=O)=CC=1>C(Cl)Cl>[OH:37][C@@H:35]([C:24]1[N:23]([C@H:20]2[CH2:21][CH2:22][C@H:17]([CH2:16][NH:15][C:45](=[O:46])[O:56][CH:57]3[CH2:61][CH2:60][O:59][CH2:58]3)[CH2:18][CH2:19]2)[C:27]2=[C:28]3[S:34][CH:33]=[CH:32][C:29]3=[N:30][CH:31]=[C:26]2[N:25]=1)[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15343685HCID 15343685, compoundHCID 178462243HCID 178462243, compound

Product 1

HCID 178462245HCID 178462245, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-1-{1-[trans-4-(aminomethyl)cyclohexyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol bis(trifluoroacetate) (18 mg, 0.032 mmol) and triethylamine (22 μL, 0.16 mmol) in methylene chloride (1 mL) was added 4-nitrophenyl tetrahydrofuran-3-yl carbonate (9.8 mg, 0.039 mmol). The mixture was stirred at room temperature for 1 h, then stripped to dryness and purified on prep-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (1.8 mg, 12%). LCMS calculated for C22H29N4O4S (M+H)+: m/z=445.2. Found: 445.0.

Workup

  1. custompurified on prep-HPLC (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-e2a621e259e34b37b672f14205fb9140
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…