N-bromobutanimide → HCID 57989938, compound

HRID 1671123Notes

Reaction equation

HRID 1671123 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:60])=[C:48]([NH:53][C:54](=[O:59])[O:55][CH2:56][CH:57]=[CH2:58])[CH:49]=[CH:50][C:51]=2[F:52])=O)[CH:40]=[CH:39][N:38]=1.C1C(=O)N(Br)C(=O)C1.[N:69]1([C:75](=[S:77])[NH2:76])[CH2:74][CH2:73][O:72][CH2:71][CH2:70]1>>[Cl:36][C:37]1[N:42]=[C:41]([C:43]2[S:77][C:75]([N:69]3[CH2:74][CH2:73][O:72][CH2:71][CH2:70]3)=[N:76][C:44]=2[C:46]2[C:47]([F:60])=[C:48]([NH:53][C:54](=[O:59])[O:55][CH2:56][CH:57]=[CH2:58])[CH:49]=[CH:50][C:51]=2[F:52])[CH:40]=[CH:39][N:38]=1

Participants

5

Reactant 4

HCID 67184N-bromobutanimideHCID 23935444-MorpholinecarbothioamideHCID 57989807N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamideHCID 579899062-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamate

Product 1

HCID 57989938HCID 57989938, compound

Procedure

Following a procedure analogous to the procedure described in Intermediate 6 using 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamate (4.0 g, 10.88 mmol), NBS (2.033 g, 11.42 mmol) and 4-morpholinecarbothioamide (1.749 g, 11.97 mmol) the title compound of Step F was obtained as a yellow solid (5.11 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.56 (br. s., 1H), 8.41-8.51 (m, 1H), 7.83 (d, J=5.9 Hz, 1H), 7.27 (t, J=8.7 Hz, 1H), 6.76 (d, J=5.3 Hz, 1H), 5.88-6.03 (m, 1H), 5.34 (d, J=17.2 Hz, 1H), 5.22 (d, J=10.1 Hz, 1H), 4.61 (d, J=5.1 Hz, 2H), 3.70-3.76 (m, 4H), 3.57 (d, J=4.4 Hz, 4H). MS (ESI): 493 [M+H]+.

Sources & evidence

ORD record
ord-8e3775ad93ea4c9daf5266701d0f3f51
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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