(S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7-methyl-2-(5'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → Methyl(2S)-2-(tert-butoxy)-2-[2-(3-{2-fluoro-4-methyl-6-[(2S)-pent-4-en-2-yloxy]phenyl}phenyl)-7-methyl-5-[4-methyl-4-(prop-2-en-1-yloxy)piperidin-1-yl]imidazo[1,2-a]pyridin-6-yl]acetate

HRID 1482042Notes

Reaction equation

[CH2:1]([O:4][C:5]1([CH3:46])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:26]5[C:31]([OH:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=5[F:34])[CH:23]=[CH:24][CH:25]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:35])[C:12]=2[C@H:36]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C:37]([O:39][CH3:40])=[O:38])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].C(O[C:51]1(C)[CH2:56][CH2:55]N(C2N3C=C(C4C=C(C5C=C(C)C=CC=5O[C@H](CC=C)C)C=CC=4)N=C3C=C(C)C=2[C@H](OC(C)(C)C)C(OC)=O)[CH2:53][CH2:52]1)C=C>>[C:42]([O:41][C@@H:36]([C:12]1[C:13]([CH3:35])=[CH:14][C:15]2[N:16]([CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[C:31]([O:32][C@H:56]([CH2:51][CH:52]=[CH2:53])[CH3:55])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=4[F:34])[CH:21]=3)[N:19]=2)[C:11]=1[N:8]1[CH2:7][CH2:6][C:5]([CH3:46])([O:4][CH2:1][CH:2]=[CH2:3])[CH2:10][CH2:9]1)[C:37]([O:39][CH3:40])=[O:38])([CH3:45])([CH3:44])[CH3:43]

Participants

Reactant 2

HCID 118308828(S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7-methyl-2-(5'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 118308851(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-fluoro-6'-hydroxy-4'-methyl-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

Product 1

HCID 118308789Methyl(2S)-2-(tert-butoxy)-2-[2-(3-{2-fluoro-4-methyl-6-[(2S)-pent-4-en-2-yloxy]phenyl}phenyl)-7-methyl-5-[4-methyl-4-(prop-2-en-1-yloxy)piperidin-1-yl]imidazo[1,2-a]pyridin-6-yl]acetateYield 90%

Procedure

Prepared in 90% yield from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′-fluoro-6′-hydroxy-4′-methyl-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate following the procedure for (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7-methyl-2-(5′-methyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. LCMS (ESI, M+1): 698.35.

Sources & evidence

ORD record: ord-bb7b2562aa11493ca501547012d5d74d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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