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 → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate

HRID 1482043Notes

Reaction equation

HRID 1482043 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:51])=[CH:13][C:14]2[N:15]([CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]4[C:42]([O:43][C@H:44]([CH2:46][CH:47]=C)[CH3:45])=[CH:41][C:40]([CH3:49])=[CH:39][C:38]=4[F:50])[CH:32]=3)[N:30]=2)[C:16]=1[N:17]1[CH2:22][CH2:21][C:20]([CH3:27])([O:23][CH2:24][CH:25]=C)[CH2:19][CH2:18]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCC=CC[C@H](C)OC2C=C(F)C=CC=2C2C=C3C=CC=2)CC1)C(OCC)=O)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:51])=[CH:13][C:14]2=[N:30][C:29]3=[CH:28][N:15]2[C:16]=1[N:17]1[CH2:18][CH2:19][C:20]([CH3:27])([O:23][CH2:24][CH:25]=[CH:47][CH2:46][C@H:44]([CH3:45])[O:43][C:42]2[CH:41]=[C:40]([CH3:49])[CH:39]=[C:38]([F:50])[C:37]=2[C:33]2[CH:32]=[C:31]3[CH:36]=[CH:35][CH:34]=2)[CH2:21][CH2:22]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

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]acetateHCID 131736663ethyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate

Product 1

HCID 123646147Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetateYield 70%

Procedure

Prepared in 70% yield from 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 following the procedure for ethyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate. LCMS (ESI, M+1): 670.25.

Sources & evidence

ORD record
ord-4da378187c3f46249ee54f6f8bff2706
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…