Triethylamine → HCID 68772803, compound

HRID 1947528Notes

Reaction equation

HRID 1947528 reaction equation
Cl.[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[O:11][C:12]1[CH:27]=[CH:26][C:15]2[CH:16]=[C:17]([CH2:19][N:20]3[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21]3)[O:18][C:14]=2[CH:13]=1.CCN(CC)CC.C[Si]([N:39]=[C:40]=[O:41])(C)C>C(Cl)Cl>[CH:14]([OH:18])=[O:41].[S:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]1[O:11][C:12]1[CH:27]=[CH:26][C:15]2[CH:16]=[C:17]([CH2:19][N:20]3[CH2:24][CH2:23][CH:22]([NH:25][C:40]([NH2:39])=[O:41])[CH2:21]3)[O:18][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 68770609HCID 68770609, compound

Product 1

HCID 68772803HCID 68772803, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-ylmethyl]-pyrrolidin-3-ylamine hydrochloride (70 mg, 0.174 mmol) in DCM (3 mL), was added Et3N (0.12 mL, 0.869 mmol), followed by trimethylsilyl isocyanate (0.19 mL, 1.39 mmol) and the resulting solution was stirred (rt, 14 h). The reaction mixture was concentrated and the resulting residue was purified by reverse phase HPLC to afford the title compound as a white solid (33 mg, 42%). MS (ESI): mass calcd. for C20H19N5O3S, 409.1; m/z found, 410.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.49 (bs, 1H), 8.31 (dd, J=8.0, 1.4, 1H), 7.74 (d, J=8.5, 1H), 7.70 (d, J=1.8, 1H), 7.38-7.32 (m, 2H), 7.10 (s, 1H), 4.36-4.29 (m, 2H), 4.33 (s, 1H), 3.52-3.38 (m, 2H), 3.25-3.14 (m, 2H), 2.45-2.34 (m, 1H), 1.99-1.89 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d7ddc16b051a4d99bedcd867a80b7c5f
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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