Acetic anhydride pyridine → HCID 58031944, compound

HRID 1429258Notes

Reaction equation

HRID 1429258 reaction equation
ClC1C=CC([C@H]2CC[C@H](C3C=CC(Cl)=C([N+]([O-])=O)C=3)N2C2C=CC(NC(C)(C)C)=C(F)C=2)=CC=1[N+]([O-])=O.[CH3:38][O:39][C:40](=[O:104])[NH:41][C@@H:42]([CH:101]([CH3:103])[CH3:102])[C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[C:50]1[NH:54][C:53]2[CH:55]=[C:56]([C@H:59]3[CH2:63][CH2:62][C@H:61]([C:64]4[CH:65]=[CH:66][C:67]5[N:71]=[C:70]([C@@H:72]6[CH2:76][CH2:75][CH2:74][N:73]6[C:77](=[O:87])[C@@H:78]([NH:82][C:83]([O:85][CH3:86])=[O:84])[CH:79]([CH3:81])[CH3:80])[NH:69][C:68]=5[CH:88]=4)[N:60]3[C:89]3[CH:94]=[CH:93][C:92]([NH:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[C:91]([F:100])[CH:90]=3)[CH:57]=[CH:58][C:52]=2[N:51]=1)=[O:44].[C:105](OC(=O)C)(=[O:107])[CH3:106].N1C=CC=CC=1>>[CH3:38][O:39][C:40](=[O:104])[NH:41][C@@H:42]([CH:101]([CH3:103])[CH3:102])[C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[C:50]1[NH:54][C:53]2[CH:55]=[C:56]([C@H:59]3[CH2:63][CH2:62][C@H:61]([C:64]4[CH:65]=[CH:66][C:67]5[N:71]=[C:70]([C@@H:72]6[CH2:76][CH2:75][CH2:74][N:73]6[C:77](=[O:87])[C@@H:78]([NH:82][C:83]([O:85][CH3:86])=[O:84])[CH:79]([CH3:81])[CH3:80])[NH:69][C:68]=5[CH:88]=4)[N:60]3[C:89]3[CH:94]=[CH:93][C:92]([N:95]([C:105](=[O:107])[CH3:106])[C:96]([CH3:97])([CH3:99])[CH3:98])=[C:91]([F:100])[CH:90]=3)[CH:57]=[CH:58][C:52]=2[N:51]=1)=[O:44]

Participants

4

Reactant 3

HCID 22348678Acetic anhydride pyridineHCID 59616977HCID 59616977, compoundHCID 86652663HCID 86652663, compound

Product 1

HCID 58031944HCID 58031944, compound

Procedure

Starting from 4-((2R,5R)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidin-1-yl)-N-tert-butyl-2-fluoroaniline, the initial product of the sequence outlined above was methyl{(2S)-1-[(2S)-2-{6-[(2R,5R)-1-[4-(tert-butylamino)-3-fluorophenyl]-5-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-benzimidazol-6-yl}pyrrolidin-2-yl]-1H-benzimidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (ACD Name v12). The N-acetyl group was added by reaction with acetic anhydride/pyridine to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.73-0.90 (m, 12 H), 1.13 (d, J=5.20 Hz, 9 H), 1.37-1.44 (m, 4 H), 1.62-1.72 (m, 2 H), 1.92-2.02 (m, 9 H), 2.10-2.26 (m, 5 H), 2.51-2.58 (m, 2 H), 3.52 (s, 6 H), 3.73-3.85 (m, 4 H), 3.98-4.12 (m, 2 H), 5.09-5.17 (m, 2 H), 5.36-5.48 (m, 3 H), 6.08-6.18 (m, 3 H), 6.74-6.87 (m, 1 H), 7.08 (dd, J=13.72, 8.29 Hz, 3 H), 7.20 (s, 1 H), 7.24-7.31 (m, 4 H), 7.40 (d, J=8.24 Hz, 1 H), 7.48 (d, J=8.13 Hz, 1 H), 12.01 (s, 1 H), 12.17 (s, 1 H); MS (ESI+) m/z 964 (M+H)+.

Sources & evidence

ORD record
ord-82c065131535496c89b4e3fa9936e125
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…