tert-Butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate → 5-(5-((2S,3S)-2-Amino-3-(4-(trifluoromethyl)phenyl)butylamino)-1,3,4-thiadiazol-2-yl)indolin-2-one

HRID 2075321Notes

Reaction equation

HRID 2075321 reaction equation
F[C:2]1[CH:3]=[C:4]([C:11]2[S:15][C:14]([N:16](C(OC(C)(C)C)=O)[CH2:17][C@@H:18]([NH:31]C(=O)OC(C)(C)C)[C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[CH3:20])=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.FC1C=C(C2SC(NC(=O)[O:63][C:64](C)(C)[CH3:65])=NN=2)C=CC=1[N+]([O-])=O.[F:69][C:70]([F:92])([F:91])[C:71]1[CH:76]=[CH:75][C:74]([C@@H:77]([C@H:79]2[CH2:83][O:82][S:81][N:80]2[C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])[CH3:78])=[CH:73][CH:72]=1>>[NH2:31][C@@H:18]([C@H:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH3:20])[CH2:17][NH:16][C:14]1[S:15][C:11]([C:4]2[CH:3]=[C:2]3[C:7](=[CH:6][CH:5]=2)[NH:8][C:64](=[O:63])[CH2:65]3)=[N:12][N:13]=1.[F:92][C:70]([F:69])([F:91])[C:71]1[CH:76]=[CH:75][C:74]([C@@H:77]([C@H:79]2[CH2:83][O:82][S:81][N:80]2[C:84]([O:86][C:87]([CH3:89])([CH3:88])[CH3:90])=[O:85])[CH3:78])=[CH:73][CH:72]=1

Participants

5

Reactant 3

HCID 57991903tert-Butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamateHCID 67089450(S)-tert-Butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylateHCID 86636672tert-butyl (2S,3S)-1-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-Boc-amino)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

Product 2

HCID 579918895-(5-((2S,3S)-2-Amino-3-(4-(trifluoromethyl)phenyl)butylamino)-1,3,4-thiadiazol-2-yl)indolin-2-oneHCID 67089450(S)-tert-Butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylate

Procedure

LCMS (API-ES) m/z (%): 448.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.41 (d, J=7.03 Hz, 3H) 2.93-3.02 (m, 1H) 3.26-3.31 (m, 4H) 3.58-3.69 (m, 1H) 6.97 (d, J=8.53 Hz, 1H) 7.51 (d, J=8.03 Hz, 2H) 7.64 (t, J=7.28 Hz, 3H) 7.70 (s, 1H). The title compound was synthesized in a similar manner as Example 2 starting with tert-butyl (2S,3S)-1-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-Boc-amino)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate, which was synthesized in a similar manner to described for Example 1 using tert-butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate to react with (S)-tert-butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylate, 2,2-dioxide. (S)-tert-Butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylate, 2,2-dioxide was synthesized as shown in Scheme 4.

Workup

  1. customwas synthesized in a similar manner

Sources & evidence

ORD record
ord-52cac502bd144c79b292a6115263990f
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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