N-bromobutanimide → HCID 57989726, compound

HRID 1961804Notes

Reaction equation

HRID 1961804 reaction equation
[Cl:1][C:2]1[C:7]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:16])[N:11]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:18][C:19](=[O:24])[O:20][CH2:21][CH:22]=[CH2:23].C1C(=O)N(Br)C(=O)C1.[N:33]1([C:39](=[S:41])[NH2:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[Cl:1][C:2]1[C:7]([C:8]2[N:40]=[C:39]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[S:41][C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:16])[N:11]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:18][C:19](=[O:24])[O:20][CH2:21][CH:22]=[CH2:23]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 23935444-MorpholinecarbothioamideHCID 86636582HCID 86636582, compound

Product 1

HCID 57989726HCID 57989726, compound

Procedure

Following a procedure analogous to the procedure described in Example 18, Step A using 2-propen-1-yl {2-chloro-3-[(2-chloro-4-pyrimidinyl)acetyl]phenyl}carbamate (3.00 g, 8.19 mmol), NBS (1.531 g, 8.60 mmol) and 4-morpholinecarbothioamide (1.677 g, 11.47 mmol) the title compound of Step C was obtained as an orange solid (4.03 g, 7.86 mmol, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.29 (s, 1H), 8.33 (d, J=5.5 Hz, 1H), 7.67-7.84 (m, 1H), 7.48 (t, J=7.8 Hz, 1H), 7.29 (dd, J=7.7, 1.5 Hz, 1H), 6.41 (d, J=5.5 Hz, 1H), 5.83-6.08 (m, 1H), 5.36 (dd, J=17.2, 1.5 Hz, 1H), 5.23 (dd, J=10.4, 1.5 Hz, 1H), 4.62 (d, J=5.3 Hz, 2H), 3.73 (t, J=4.8 Hz, 4H), 3.57 (t, J=4.8 Hz, 4H). MS (ESI): 491.98 [M+H]+.

Sources & evidence

ORD record
ord-00209998a7e443e4bd31f5b7ef32d66d
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

Loading…