N-bromobutanimide → HCID 57989895, compound

HRID 1671226Notes

Reaction equation

HRID 1671226 reaction equation
ClC1N=C(C2SC(C(C)(C)C)=NC=2C2C=C(NS(C3C=C(F)C=CC=3F)(=O)=O)C=CC=2)C=CN=1.[Cl:35][C:36]1[N:41]=[C:40]([CH2:42][C:43]([C:45]2[C:46]([F:63])=[C:47]([NH:51][S:52]([C:55]3[C:60]([F:61])=[CH:59][CH:58]=[CH:57][C:56]=3[F:62])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=2)=O)[CH:39]=[CH:38][N:37]=1.C1C(=O)N(Br)C(=O)C1.[OH:72][CH2:73][C:74]([CH3:79])([CH3:78])[C:75](=[S:77])[NH2:76]>>[Cl:35][C:36]1[N:41]=[C:40]([C:42]2[S:77][C:75]([C:74]([CH3:79])([CH3:78])[CH2:73][OH:72])=[N:76][C:43]=2[C:45]2[C:46]([F:63])=[C:47]([NH:51][S:52]([C:55]3[C:60]([F:61])=[CH:59][CH:58]=[CH:57][C:56]=3[F:62])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=2)[CH:39]=[CH:38][N:37]=1

Participants

5

Reactant 4

HCID 67184N-bromobutanimideHCID 55285806HCID 55285806, compoundHCID 57989720N-(3-(2-(2-chloropyriMidin-4-yl)acetyl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamideHCID 57989961N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamide

Product 1

HCID 57989895HCID 57989895, compound

Procedure

Following a procedure analogous to the procedure described for Intermediate 9 using N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (750 mg, 1.7 mmol), NBS (317 mg, 1.782 mmol), and 3-hydroxy-2,2-dimethylpropanethioamide (248 mg, 1.86 mmol), the title compound was obtained as an yellow foam (460 mg, 45%). A portion of the sample was crystallized from ethyl acetate-hexanes. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.92 (s, 1H) 8.54 (d, J=5.31 Hz, 1H) 7.64-7.74 (m, 1H) 7.41-7.50 (m, 2H) 7.31-7.36 (m, 1H) 7.24 (t, J=8.97 Hz, 2H) 6.87 (d, J=5.31 Hz, 1H) 5.2-5.4 (br s, 1H) 3.54 (s, 2H) 1.36 (s, 6H). MS (ESI): 555.0 [M+H]+.

Sources & evidence

ORD record
ord-2656a4e99f154f8693ca5af8220531a3
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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