N-bromobutanimide → HCID 57989648, compound

HRID 1671113Notes

Reaction equation

HRID 1671113 reaction equation
ClC1N=C(C2SC(N3CCCC3)=NC=2C2C=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=CC=2)C=CN=1.[Cl:36][C:37]1[N:42]=[C:41]([CH2:43][C:44]([C:46]2[C:47]([F:64])=[C:48]([NH:52][S:53]([C:56]3[C:61]([F:62])=[CH:60][CH:59]=[CH:58][C:57]=3[F:63])(=[O:55])=[O:54])[CH:49]=[CH:50][CH:51]=2)=O)[CH:40]=[CH:39][N:38]=1.C1C(=O)N(Br)C(=O)C1.[N:73]1([C:81](=[S:83])[NH2:82])[CH2:78][CH2:77][S:76](=[O:80])(=[O:79])[CH2:75][CH2:74]1>>[Cl:36][C:37]1[N:42]=[C:41]([C:43]2[S:83][C:81]([N:73]3[CH2:78][CH2:77][S:76](=[O:80])(=[O:79])[CH2:75][CH2:74]3)=[N:82][C:44]=2[C:46]2[C:47]([F:64])=[C:48]([NH:52][S:53]([C:56]3[C:61]([F:62])=[CH:60][CH:59]=[CH:58][C:57]=3[F:63])(=[O:55])=[O:54])[CH:49]=[CH:50][CH:51]=2)[CH:40]=[CH:39][N:38]=1

Participants

5

Reactant 4

HCID 67184N-bromobutanimideHCID 43581571HCID 43581571, compoundHCID 57989720N-(3-(2-(2-chloropyriMidin-4-yl)acetyl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamideHCID 57989807N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 57989648HCID 57989648, compoundYield 90%

Procedure

Following a procedure analogous to Intermediate 6 using N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (1.5 g, 3.40 mmol), NBS (0.60 g, 3.40 mmol) and 4-thiomorpholinecarbothioamide 1,1-dioxide (0.80 g, 4.12 mmol) the title compound of Step A was obtained (1.88 g, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.94 (br. s., 1H), 8.34 (d, J=5.1 Hz, 1H), 7.59-7.78 (m, 1H), 7.37-7.52 (m, 2H), 7.32 (t, J=7.7 Hz, 1H), 7.25 (t, J=9.1 Hz, 2H), 6.55 (d, J=4.9 Hz, 1H), 4.04 (br. s., 4H), 3.32 (br. s., 4H). m/z (ES+): 617 [M+H]+.

Sources & evidence

ORD record
ord-3209220b62684133b8acc073f82c8ec2
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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