N,N,N',N'-Tetramethylazodicarboxamide → HCID 45111663, compound

HRID 1678677Notes

Reaction equation

HRID 1678677 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:18][OH:19])=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]([C:30]1([O:33][C:34]2[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=2)[CH2:32][CH2:31]1)=[O:29].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>C1COCC1>[CH3:26][O:27][C:28]([C:30]1([O:33][C:34]2[CH:39]=[CH:38][C:37]([O:19][CH2:18][CH:17]([C:16]3[N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=[C:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]4)[CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:36][CH:35]=2)[CH2:32][CH2:31]1)=[O:29]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 67131197HCID 67131197, compoundHCID 67131209HCID 67131209, compound

Product 1

HCID 45111663HCID 45111663, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to the procedure described in example 29.2, 2-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-2-cyclohexyl-ethanol (example 29.1) was reacted with 1-(4-hydroxy-phenoxy)-cyclopropanecarboxylic acid methyl ester (Hazeldine, Stuart T.; Polin, Lisa; Kushner, Juiwanna; White, Kathryn; Corbett, Thomas H.; Horwitz, Jerome P. Bioorganic & Medicinal Chemistry (2005), 13(12), 3910-3920) in the presence of tri-n-butylphosphine and N,N,N′,N′-tetramethylazodicarboxamide in THF at ambient temperature to give the title compound as off-white solid. MS: m/e=545.3 [M+H+].

Sources & evidence

ORD record
ord-76b203b3588e40f5b91fa3ec969af34d
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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