Dimethylformamide → HCID 69597852, compound

HRID 724728Notes

Reaction equation

HRID 724728 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].Br[C:9]1[CH:10]=[C:11]([CH2:23][C@H:24]([NH:36][S:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:39])=[O:38])[C:25]2[NH:26][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][N:29]=2)[CH:12]=[CH:13][C:14]=1[CH:15]1[S:19](=[O:21])(=[O:20])[NH:18][C:17](=[O:22])[CH2:16]1.[CH3:46][N:47](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:46]([C:9]1[CH:10]=[C:11]([CH2:23][C@H:24]([NH:36][S:37]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)(=[O:39])=[O:38])[C:25]2[NH:26][C:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:28][N:29]=2)[CH:12]=[CH:13][C:14]=1[CH:15]1[S:19](=[O:20])(=[O:21])[NH:18][C:17](=[O:22])[CH2:16]1)#[N:47]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 69597890HCID 69597890, compound

Product 1

HCID 69597852HCID 69597852, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of N-[(1S)-2-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-1-(5-phenyl-1H-imidazol-2-yl)ethyl]benzenesulfonamide trifluoroacetate (3.5 mg, 4.8 μmol), zinc cyanide (1.7 mg, 14 μmol), tetrakis(triphenylphosphine)palladium(0) (1.11 mg, 960 nmol) and N,N-dimethylformamide (1.5 mL) was heated at 175° C. for 4 min in the microwave. The reaction filtered, concentrated in vacuo and purified by preparative LCMS to yield the desired product (2.0 mg, 60%). 1H NMR (400 MHz, CD3OD): δ 7.8–7.3 (m, 13H), 5.3–5.0 (m, 2H), 3.5–3.4 (m, 2H), 3.3–3.2 (m, 2H); MF=C29H24F3N5O7S2; LCMS found for C27H24N5O5S2(M+H)+: m/z=562.

Workup

  1. filtrationThe reaction filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-c518d8ec01df48e5ae14a83dc02924e6
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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