(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → (2S)-2-(tert-Butoxy)-2-{4,28-dimethyl-21,27,33-trioxa-1,7,11,12,34-pentaazahexacyclo[26.2.2.16,9.110,13.02,7.015,20]tetratriaconta-2,4,6(34),8,10,12,15(20),16,18-nonaen-3-yl}acetic acid

HRID 1481989Notes

Reaction equation

[CH2:1]([O:4][C:5]1([CH3:48])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]4[O:21][C:22]([CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:32][CH2:33][CH2:34][CH:35]=C)=[N:23][N:24]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:37])[C:12]=2[C@H:38]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:39]([O:41]C)=[O:40])[CH2:7][CH2:6]1)[CH:2]=C.C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCCCCCOC2C=CC(F)=CC=2CNC3=O)CC1)C(OC)=O)(C)(C)C.C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCCCCCOC2C=CC(F)=CC=2CNC3=O)CC1)C(O)=O)(C)(C)C>>[C:44]([O:43][C@@H:38]([C:12]1[C:13]([CH3:37])=[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]([CH3:48])([O:4][CH2:1][CH2:2][CH2:35][CH2:34][CH2:33][O:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][C:22]2[O:21][C:20]3=[N:24][N:23]=2)[CH2:10][CH2:9]1)[C:39]([OH:41])=[O:40])([CH3:46])([CH3:45])[CH3:47]

Participants

Reactant 3

HCID 118308913(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 118316265Methyl(2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetate

HCID 118316266(2S)-2-(tert-Butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acid

Product 1

HCID 118316267(2S)-2-(tert-Butoxy)-2-{4,28-dimethyl-21,27,33-trioxa-1,7,11,12,34-pentaazahexacyclo[26.2.2.16,9.110,13.02,7.015,20]tetratriaconta-2,4,6(34),8,10,12,15(20),16,18-nonaen-3-yl}acetic acidYield 6%

Procedure

Prepared from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5-(2-(but-3-en-1-yloxy)benzyl)-1,3,4-oxadiazol-2-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate in 6% yield following the procedures used to prepare methyl(2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetate and (2S)-2-(tert-butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19,25-dioxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acid. 1H NMR (500 MHz, DMSO-d6) δ 8.08-8.03 (m, 1H), 7.36-7.32 (m, 2H), 7.28-7.23 (m, 1H), 7.09-7.01 (m, 1H), 6.97-6.89 (m, 1H), 5.92-5.76 (m, 1H), 4.33-4.21 (m, 2H), 4.13-4.03 (m, 2H), 3.77-3.69 (m, 2H), 3.14-3.03 (m, 2H), 2.91-2.81 (m, 1H), 2.74-2.62 (m, 1H), 2.44-2.39 (m, 3H), 1.93-1.60 (m, 10H), 1.23-1.20 (m, 3H), 1.17 (s, 9H); LCMS (ESI, M+1): 618.5.

Sources & evidence

ORD record: ord-21795edc9d7349a1a7f4c5083d74acb3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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