HCID 178452515, compound → HCID 178495672, compound

HRID 1751734Notes

Reaction equation

HRID 1751734 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9](=[O:22])[C@H:10]([NH:17][C:18](=[O:21])[O:19][CH3:20])[C:11]2[CH:16]=CC=C[CH:12]=2)[C@H:6]([C:23]2[NH:27][C:26]3[C:28]4[C:33]([CH:34]=[CH:35][C:25]=3[N:24]=2)=[CH:32][C:31]([C:36]2[CH:37]=[C:38]3[C:63](=[CH:64][CH:65]=2)[C:42]2[NH:43][C:44]([C@@H:46]5[CH2:51][C@@H:50]6[C@@H:48]([CH2:49]6)[N:47]5[C:52](=[O:62])[C@@H:53]([NH:57][C:58]([O:60][CH3:61])=[O:59])[CH:54]([CH3:56])[CH3:55])=[N:45][C:41]=2[CH:40]=[CH:39]3)=[CH:30][CH:29]=4)[CH2:5]1.CO[CH2:68][C@@H:69]1CN(C(=O)[C@@H](NC(=O)OC)C(C)C)[C@H](C2NC3C4C(C=CC=3N=2)=CC(B2OC(C)(C)C(C)(C)O2)=CC=4)[CH2:70]1.CC1(C)C(C)(C)OB(C2C=C3C(=CC=2)C2NC([C@@H]4C[C@@H]5[C@@H](C5)N4C(OC(C)(C)C)=O)=NC=2C=C3)O1>>[CH3:61][O:60][C:58]([NH:57][C@H:53]([C:54]1[CH:55]=[CH:70][CH:69]=[CH:68][CH:56]=1)[C:52]([N:47]1[C@H:46]([C:44]2[NH:43][C:42]3[C:63]4[C:38](=[CH:37][C:36]([C:31]5[CH:32]=[C:33]6[C:28](=[CH:29][CH:30]=5)[C:26]5[NH:27][C:23]([C@@H:6]7[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[CH2:8][N:7]7[C:9](=[O:22])[C@@H:10]([NH:17][C:18](=[O:21])[O:19][CH3:20])[CH:11]([CH3:16])[CH3:12])=[N:24][C:25]=5[CH:35]=[CH:34]6)=[CH:65][CH:64]=4)[CH:39]=[CH:40][C:41]=3[N:45]=2)[CH2:51][C@@H:50]2[C@H:48]1[CH2:49]2)=[O:62])=[O:59]

Participants

4

Reactant 3

HCID 178452515HCID 178452515, compoundHCID 178495667HCID 178495667, compoundHCID 178495673HCID 178495673, compound

Product 1

HCID 178495672HCID 178495672, compoundYield 27%

Procedure

This compound was made using the same procedure as was used to make methyl (R)-2-((2S,4S)-4-(methoxymethyl)-2-(2′-((1R,3S,5R)-2-((S)-3-methyl-2-methoxycarbonylaminobutanoyl)-2-azabicyclo[3.1.0]hexan-3-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate, using methyl (S)-1-((2S,4S)-4-(methoxymethyl)-2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate and (1R,3S,5R)-tert-butyl 3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate in the Suzuki-Miyaura cross coupling to give methyl (S)-1-((2S,4S)-2-(2′-((1R,3S,5R)-2-((R)-2-(methoxycarbonylamino)-2-phenylacetyl)-2-azabicyclo[3.1.0]hexan-3-yl)-1H,1′H-7,7′-binaphtho[2,1-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (0.048 g, 27%). MS (ESI) m/z 877.71 [M+H]. 1H NMR (400 MHz, cd3od) δ 8.68-8.50 (m, 2H), 8.42-8.23 (m, 2H), 8.14-7.90 (m, 2H), 7.86-7.67 (m, 3H), 7.62-7.51 (m, J=6.2 Hz, 2H), 7.49-7.39 (m, J=15.3, 7.6 Hz, 2H), 6.86-6.01 (m, 5H), 5.83-5.67 (m, 1H), 5.59 (s, 1H), 5.49-5.33 (m, 2H), 4.64-4.18 (m, 3H), 4.13-3.92 (m, 2H), 3.87-3.76 (m, J=7.2 Hz, 2H), 3.68 (s, 2H), 2.89-2.22 (m, 7H), 2.19-2.00 (m, 3H), 1.77-1.48 (m, 2H), 1.11-0.85 (m, 7H), 0.80-0.68 (m, J=4.5 Hz, 2H).

Sources & evidence

ORD record
ord-c5301c0f5a084ee0a12d0d9a5adb8e7c
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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