Diisopropylethylamine → HCID 117732279, compound

HRID 1772650Notes

Reaction equation

HRID 1772650 reaction equation
[C:1]([O:5][C:6]([N-:8][S:9]([N:12]1[CH:17]=[CH:16][C:15](=[N+](C)C)[CH:14]=[CH:13]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O1CCN(C2C3N(C=C(/C=C/C4C=CC5C(=CC=CC=5)N=4)N=3)C(C3C=CC(N4CCC(C(O)=O)CC4)=CC=3)=CN=2)CC1.FC(F)(F)C(O)=O.N1CCC([C:83]2[N:88]3[CH:89]=[C:90]([CH2:92][O:93][C:94]4[CH:103]=[CH:102][C:101]5[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=5)[N:95]=4)[N:91]=[C:87]3[C:86]([N:104]3[CH2:109][CH2:108][O:107][CH2:106][CH2:105]3)=[N:85][CH:84]=2)CC1.CCN(C(C)C)C(C)C>C(Cl)Cl>[O:107]1[CH2:108][CH2:109][N:104]([C:86]2[C:87]3[N:88]([CH:89]=[C:90]([CH2:92][O:93][C:94]4[CH:103]=[CH:102][C:101]5[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=5)[N:95]=4)[N:91]=3)[C:83]([CH:15]3[CH2:14][CH2:13][N:12]([S:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:10])=[O:11])[CH2:17][CH2:16]3)=[CH:84][N:85]=2)[CH2:105][CH2:106]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 86345566HCID 86345566, compoundHCID 117728084HCID 117728084, compoundHCID 178482962HCID 178482962, compound

Product 1

HCID 117732279HCID 117732279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (38 mg, 0.12 mmol, prepared according to the Org. Lett., 2001, 3 (14), pp 2241-2243) was added to a solution of compound 111 (100 mg, 0.12 mmol, Example 26) and DIEA (54 μL, 0.38 mmol) in DCM (1 mL). The resulting mixture was stirred at rt for 3 h and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:1-1:0 EtAOc/hexane) to obtain compound 28a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C30H37N7O6S: 624.2 (M+H). Found 624.2.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas purified by flash column chromatography on silica gel (0:1-1:0 EtAOc/hexane)

Sources & evidence

ORD record
ord-b8e1efd08b5d4a048a5343951dfefdf5
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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