HCID 66615052, compound → HCID 46199992, compound

HRID 717694Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:31]C(=O)OC(C)(C)C)([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]4[N:21]=[C:20](/[CH:22]=[CH:23]/[C:24]5[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=5)[O:19][N:18]=4)=[CH:13][C:11]=3[CH:12]=2)[CH2:4][O:3]1.C(=O)(OC1(C2OC3C=CC(C4N=C(C5C=CC(OCCC)=C(Cl)C=5)ON=4)=CC=3C=2)COC(C)(C)OC1C(C)(C)C)N>>[NH2:31][C:5]([C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]=[C:20](/[CH:22]=[CH:23]/[C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[O:19][N:18]=3)=[CH:13][C:11]=2[CH:12]=1)([CH2:4][OH:3])[CH2:6][OH:7]

Participants

Reactant 2

HCID 66615052HCID 66615052, compound

HCID 86711965HCID 86711965, compound

Product 1

HCID 46199992HCID 46199992, compoundYield 48%

Procedure

When the product of Step C was substituted for tert-butyl5-(5-(5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-yl carbamate in Example 36, Step E, the similar procedure afforded the title compound in 48% yield, as colourless solid. 1H-NMR (DMSO-d6) 8.23 (b, 1H); 7.9-7.85 (m, 2H); 7.72-7.64 (m, 3H); 7.33 (d, 1H, J=16.2 Hz); 7.25 (d, 2H, J=6.3 Hz); 6.87 (s, 1H); 4.77 (b, 2H); 3.63 (b, 2H); 3.56 (b, 2H); 2.32 (s, 3H); 1.95 (b, 2H).

Sources & evidence

ORD record: ord-68f837335c814d2c9aad15db42cd27a8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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