Triphenylphosphine → tert-Butyl 4-{4-[2-(7-isoquinolinyloxy)ethoxy]-1,2,5-thiadiazol-3-yl}-1-piperazinecarboxylate

HRID 991701Notes

Reaction equation

HRID 991701 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:7][S:8][N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:43]1[CH:52]=[C:51]2[C:46]([CH:47]=[CH:48][N:49]=[CH:50]2)=[CH:45][CH:44]=1.N(C(OCC)=O)=NC(OCC)=O>>[CH:50]1[C:51]2[C:46](=[CH:45][CH:44]=[C:43]([O:1][CH2:2][CH2:3][O:4][C:5]3[C:6]([N:10]4[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]4)=[N:7][S:8][N:9]=3)[CH:52]=2)[CH:47]=[CH:48][N:49]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4597677-IsoquinolinolHCID 22036393tert-Butyl 4-[4-(2-hydroxyethoxy)-1,2,5-thiadiazol-3-yl]-1-piperazinecarboxylate

Product 1

HCID 22036525tert-Butyl 4-{4-[2-(7-isoquinolinyloxy)ethoxy]-1,2,5-thiadiazol-3-yl}-1-piperazinecarboxylate

Procedure

The title compound was prepared according to the procedure of Example 218, Step 3 starting from the product of Example 218, Step 2 (100 mg, 0.30 mmol), triphenylphosphine (102 mg, 0.39 mmol), 7-hydroxyisoquinoline (57 mg, 0.39 mmol) and diethyl azodicarboxylate (61 μl, 0.39 mmol) except that the reaction mixture was stirred at room temperature for 5 days. It gave an orange oil (0.34 g) of low purity (63% by HPLC). It was used directly in the following step without further purification.

Sources & evidence

ORD record
ord-85ca45a7e9564c159150a9897b8ca019
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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