HCID 86725310, compound → HCID 76684257, compound

HRID 925196Notes

Reaction equation

HRID 925196 reaction equation
C(OC([N:6]1[CH2:21][CH2:20][C:10]2[C:11]3[C:12](=O)[CH2:13][CH2:14][C:15]=3[C:16]([Cl:18])=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[CH2:22]([Mg]Br)[CH3:23]>>[Cl:18][C:16]1[C:15]2[CH2:14][CH2:13][CH:12]([CH2:22][CH3:23])[C:11]=2[C:10]2[CH2:20][CH2:21][NH:6][CH2:7][CH2:8][C:9]=2[CH:17]=1

Participants

3

Reactant 2

HCID 86725310HCID 86725310, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 76684257HCID 76684257, compound

Procedure

Example 6 was prepared in a similar fashion to Example 4, except Intermediate 4 was used as the starting material and ethylmagnesium bromide (3M in diethyl ether) was used instead of cyclopropylmagnesium bromide (Example 4, step (a)). 1H NMR (300 MHz, CDCl3) δ 6.92 (s, 1H); 3.16-3.09 (m, 1H); 2.98-2.84 (m, 10H); 2.37-2.32 (br s, 1H); 2.17-1.94 (m, 2H); 1.47-1.25 (m, 2H); 0.95 (t, J=7.5 Hz, 3H); MS: ESI (positive): 250, (M+1).

Sources & evidence

ORD record
ord-6a691e4cabaa4acb90b5f3e3b081dfc1
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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