Acetic anhydride pyridine → HCID 58031944, compound

HRID 1411438Notes

Reaction equation

HRID 1411438 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.[C:38]([NH:42][C:43]1[CH:48]=[CH:47][C:46]([N:49]2[C@@H:53]([C:54]3[CH:55]=[CH:56][C:57]4[N:61]=[C:60]([C@@H:62]5[CH2:66][CH2:65][CH2:64][N:63]5[C:67](=[O:77])[C@@H:68]([NH:72][C:73]([O:75][CH3:76])=[O:74])[CH:69]([CH3:71])[CH3:70])[NH:59][C:58]=4[CH:78]=3)[CH2:52][CH2:51][C@@H:50]2[C:79]2[CH:80]=[CH:81][C:82]3[N:86]=[C:85]([C@@H:87]4[CH2:91][CH2:90][CH2:89][N:88]4[C:92](=[O:102])[C@@H:93]([NH:97][C:98](=[O:101])[O:99][CH3:100])[CH:94]([CH3:96])[CH3:95])[NH:84][C:83]=3[CH:103]=2)=[CH:45][C:44]=1[F:104])([CH3:41])([CH3:40])[CH3:39].[C:105](OC(=O)C)(=[O:107])[CH3:106].N1C=CC=CC=1>>[C:105]([N:42]([C:38]([CH3:41])([CH3:39])[CH3:40])[C:43]1[CH:48]=[CH:47][C:46]([N:49]2[C@@H:53]([C:54]3[CH:55]=[CH:56][C:57]4[N:61]=[C:60]([C@@H:62]5[CH2:66][CH2:65][CH2:64][N:63]5[C:67](=[O:77])[C@@H:68]([NH:72][C:73]([O:75][CH3:76])=[O:74])[CH:69]([CH3:71])[CH3:70])[NH:59][C:58]=4[CH:78]=3)[CH2:52][CH2:51][C@@H:50]2[C:79]2[CH:80]=[CH:81][C:82]3[N:86]=[C:85]([C@@H:87]4[CH2:91][CH2:90][CH2:89][N:88]4[C:92](=[O:102])[C@@H:93]([NH:97][C:98](=[O:101])[O:99][CH3:100])[CH:94]([CH3:96])[CH3:95])[NH:84][C:83]=3[CH:103]=2)=[CH:45][C:44]=1[F:104])(=[O:107])[CH3:106]

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, 12H), 1.13 (d, J=5.20 Hz, 9H), 1.37-1.44 (m, 4H), 1.62-1.72 (m, 2H), 1.92-2.02 (m, 9H), 2.10-2.26 (m, 5H), 2.51-2.58 (m, 2H), 3.52 (s, 6H), 3.73-3.85 (m, 4H), 3.98-4.12 (m, 2H), 5.09-5.17 (m, 2H), 5.36-5.48 (m, 3H), 6.08-6.18 (m, 3H), 6.74-6.87 (m, 1H), 7.08 (dd, J=13.72, 8.29 Hz, 3H), 7.20 (s, 1H), 7.24-7.31 (m, 4H), 7.40 (d, J=8.24 Hz, 1H), 7.48 (d, J=8.13 Hz, 1H), 12.01 (s, 1H), 12.17 (s, 1H); MS (ESI+) m/z 964 (M+H)+.

Sources & evidence

ORD record
ord-51fedb32f73044449e52b15316ed3ff6
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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