HCID 86725310, compound → HCID 76684261, compound

HRID 925199Notes

Reaction equation

HRID 925199 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.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Cl:18][C:16]1[C:15]2[CH2:14][CH2:13][CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[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 178418255HCID 178418255, compound

Product 1

HCID 76684261HCID 76684261, compound

Procedure

Example 10 was prepared in a similar fashion to Example 4, except Intermediate 4 was used as the starting material and phenylmagnesium bromide (3M in diethyl ether) was used instead of cyclopropylmagnesium bromide (Example 4, step (a)). NMR (300 MHz, CDCl3) δ 7.26-7.21 (m, 2H); 7.19-7.13 (m, 1H); 7.01 (s, 1H); 6.99-6.96 (m, 2H); 4.51-4.47 (m, 1H); 3.07-2.82 (m, 6H); 2.69-2.53 (m, 4H); 2.47-2.42 (m, 1H); 2.24-2.17 (m, 1H); 2.08-2.05 (m, 1H); MS: ESI (positive): 298, (M+1).

Sources & evidence

ORD record
ord-616546ee164d45b0a8e623b309c02257
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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