HCID 86661813, compound → HCID 46195747, compound

HRID 710483Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:32]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][C:20]4[O:21][C:22]5[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH3:31])=[CH:25][C:23]=5[CH:24]=4)=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OCCCC)(CN2C3C(=C(C4N=C(C5C=NC(CCC)=CC=5)ON=4)C=CC=3)CC2)CO1>>[NH2:32][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][C:20]3[O:21][C:22]4[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH3:31])=[CH:25][C:23]=4[CH:24]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

Reactant 2

HCID 86661813HCID 86661813, compound

HCID 86661814HCID 86661814, compound

Product 1

HCID 46195747HCID 46195747, compoundYield 45%

Procedure

When the product of Step D was substituted for tea-butyl 2,2-dimethyl-5-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate in Example 66, Step F, the identical process afforded the title compound in 45% yield, as colourless solid. 1H-NMR (CDCl3+CD3OD) 0.92 (tr, 3H, J=6 Hz); 1.56-1.67 (m, 2H+H2O); 2.55-2.65 (m, 2H); 2.91 (tr, 2H, J=(Hz); 2.98 (s, 2H); 3.39 (tr, 2H, J=6 Hz); 3.4-3.6 (m, 4H); 5.02 (s, 2H); 6.5 (d, 1H, J=9 Hz); 6.64 (s, 1H); 6.68-6.81 (m, 2H); 7.06 (dd, 1H, J=3, 9 Hz); 7.28-7.37 (m, 2H).

Sources & evidence

ORD record: ord-45bb545abda34a10b510096af211685f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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