Ethanol → HCID 68227352, compound

HRID 1808902Notes

Reaction equation

HRID 1808902 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[OH:28])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:29][C:30](=[O:40])[C:31]2[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=2)=[C:4]([N+:41]([O-:43])=[O:42])[CH:3]=1.[CH2:44](O)[CH3:45].C(P(CCCC)CCCC)CCC.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH2:44][CH3:45])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:29][C:30](=[O:40])[C:31]2[CH:36]=[CH:35][C:34]([N:37]([CH3:38])[CH3:39])=[CH:33][CH:32]=2)=[C:4]([N+:41]([O-:43])=[O:42])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 13831TributylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 136116857HCID 136116857, compound

Product 1

HCID 68227352HCID 68227352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of N-(4-chloro-5-(4-(3-(2-hydroxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-(dimethylamino)benzamide (Example 117, 17 mg, 0.028 mmol), ethanol (2.461 μL, 0.042 mmol) and tri-n-butyl phosphine (10.40 μL, 0.042 mmol) in THF (2 mL) at 0° C. was added DIAD (8.19 μL, 0.042 mmol). The reaction mixture was stirred at 0° C. for 3 min. and at RT overnight.

Sources & evidence

ORD record
ord-e05378299716479c8c592382effb0191
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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