(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-4'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-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 1482038Notes

Reaction equation

[CH2:1]([O:4][C:5]1([CH3:51])[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[CH:31]=[C:30]([F:32])[C:29]([CH3:33])=[CH:28][C:27]=5[O:34][C@H:35]([CH2:37][CH:38]=[CH2:39])[CH3:36])[CH:23]=[CH:24][CH:25]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:40])[C:12]=2[C@H:41]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:42]([O:44][CH3:45])=[O:43])[CH2:7][CH2:6]1)C=C.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:47]([O:46][C@@H:41]([C:12]1[C:13]([CH3:40])=[CH:14][C:15]2=[N:19][C:18]3=[CH:17][N:16]2[C:11]=1[N:8]1[CH2:7][CH2:6][C:5]([CH3:51])([O:4][CH2:1][CH:39]=[CH:38][CH2:37][C@H:35]([CH3:36])[O:34][C:27]2[CH:28]=[C:29]([CH3:33])[C:30]([F:32])=[CH:31][C:26]=2[C:22]2[CH:21]=[C:20]3[CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)[C:42]([O:44][CH3:45])=[O:43])([CH3:48])([CH3:49])[CH3:50]

Participants

Reactant 2

HCID 118308875(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-4'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 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 123141276Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-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 82%

Procedure

Prepared in 82% yield from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5′-fluoro-4′-methyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)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. 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=7.8 Hz, 1H), 8.08 (s, 1H), 8.04 (s, 1H), 7.54-7.49 (m, 1H), 7.32 (s, 1H), 7.29 (d, J=1.3 Hz, 1H), 7.03 (d, J=10.3 Hz, 1H), 6.83 (d, J=6.5 Hz, 1H), 6.25-6.14 (m, 1H), 6.05 (br. s., 1H), 5.86-5.75 (m, 1H), 4.51-4.40 (m, 1H), 4.10-3.93 (m, 3H), 3.78 (t, J=10.9 Hz, 1H), 3.69 (s, 3H), 3.07 (d, J=7.8 Hz, 1H), 2.69 (d, J=7.5 Hz, 1H), 2.51-2.47 (m, 1H), 2.46 (s, 3H), 2.41-2.35 (m, 1H), 2.32 (d, J=1.5 Hz, 3H), 1.98 (t, J=12.8 Hz, 2H), 1.82-1.70 (m, 2H), 1.33 (s, 3H), 1.25 (s, 9H), 1.06 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1): 670.25.

Sources & evidence

ORD record: ord-ff8cfb0abfcf4e8895a9ae52fc338763
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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