4-(2-Bromoethyl)morpholine → (1aR,5S,8S,10R,22aR)-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-17-[2-(morpholin-4-yl)ethoxy]-3,6-dioxo-14-(propan-2-yl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide

HRID 522396Notes

Reaction equation

HRID 522396 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[C:10]([C@H:14]1[C:44](=[O:45])[N:43]2[CH2:46][C@@H:40]([CH2:41][C@H:42]2[C:47]([NH:49][C@:50]2([C:55](=[O:64])[NH:56][S:57]([C:60]3([CH3:63])[CH2:62][CH2:61]3)(=[O:59])=[O:58])[CH2:52][C@H:51]2[CH:53]=[CH2:54])=[O:48])[O:39][C:26]2=[N:27][C:28]3[CH:29]=[C:30]([CH:36]([CH3:38])[CH3:37])[CH:31]=[CH:32][C:33]=3[C:34]([OH:35])=[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:65][C@H:18]2[O:17][C:16](=[O:66])[NH:15]1)([CH3:13])([CH3:12])[CH3:11]>>[C:10]([C@H:14]1[C:44](=[O:45])[N:43]2[CH2:46][C@@H:40]([CH2:41][C@H:42]2[C:47]([NH:49][C@:50]2([C:55](=[O:64])[NH:56][S:57]([C:60]3([CH3:63])[CH2:62][CH2:61]3)(=[O:59])=[O:58])[CH2:52][C@H:51]2[CH:53]=[CH2:54])=[O:48])[O:39][C:26]2=[N:27][C:28]3[CH:29]=[C:30]([CH:36]([CH3:38])[CH3:37])[CH:31]=[CH:32][C:33]=3[C:34]([O:35][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)=[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:65][C@H:18]2[O:17][C:16](=[O:66])[NH:15]1)([CH3:12])([CH3:13])[CH3:11]

Participants

3

Reactant 2

HCID 15021014-(2-Bromoethyl)morpholineHCID 178455700HCID 178455700, compound

Product 1

HCID 117598835(1aR,5S,8S,10R,22aR)-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-17-[2-(morpholin-4-yl)ethoxy]-3,6-dioxo-14-(propan-2-yl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide

Procedure

The title compound was prepared using the same method as described in Example 42, using the 4-(2-bromoethyl)morpholine and (1aR,5S,8S,10R,22aR)-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-17-hydroxy-3,6-dioxo-14-(propan-2-yl)-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide (synthesized in the same way as Example 120 but using intermediates A2, B10 and C9). LRMS (ES+) m/z 921.55 (M+H)+.

Workup

  1. customsynthesized in the same way as Example 120

Sources & evidence

ORD record
ord-c62e54986341462c94e2aa4deac2eaee
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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