2-Chloro-4-methylpyrimidine → HCID 136188919, compound

HRID 1670980Notes

Reaction equation

HRID 1670980 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=C(/C2C=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=CC=2)\O)[CH:5]=[CH:4][N:3]=1.[Cl:29][C:30]1[C:39]([NH:40][C:41]([O:43][CH2:44][CH:45]=[CH2:46])=[O:42])=[CH:38][CH:37]=[CH:36][C:31]=1[C:32]([O:34]C)=O.ClC1N=C(C)C=CN=1>>[Cl:29][C:30]1[C:31](/[C:32](/[OH:34])=[CH:8]\[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:36][CH:37]=[CH:38][C:39]=1[NH:40][C:41](=[O:42])[O:43][CH2:44][CH:45]=[CH2:46]

Participants

4

Reactant 3

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989809HCID 57989809, compoundHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 136188919HCID 136188919, compoundYield 79.6%

Procedure

Following a procedure analogous to the procedure described in Intermediate 5, Step B using methyl 2-chloro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (30 g, 0.11 mol) and 2-chloro-4-methylpyrimidine (15.8 g, 0.12 mol) the title compound of Step B was prepared (29 g, 79.6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.52-13.58 (br, 0.9H), 8.41-8.42 (m, 1H), 8.22-8.27 (m, 1H), 7.28-7.35 (m, 2.2H), 7.21-7.24 (m, 1.2H), 6.85-6.88 (m, 1H), 5.91-6.02 (m, 1H), 5.73 (s, 1H), 5.23-5.40 (m, 2H), 4.66-4.70 (m, 2H).

Sources & evidence

ORD record
ord-e38a781854794a9f8d2a2e6e0cabdaf7
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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