Furan-2-sulfonyl Chloride → HCID 57989968, compound

HRID 590087Notes

Reaction equation

HRID 590087 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[N:9]=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:26].[O:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[S:32](Cl)(=[O:34])=[O:33]>>[Cl:1][C:2]1[C:7]([C:8]2[N:9]=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[N:14]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:26][S:32]([C:28]1[O:27][CH:31]=[CH:30][CH:29]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 2795072Furan-2-sulfonyl ChlorideHCID 57989989HCID 57989989, compound

Product 1

HCID 57989968HCID 57989968, compound

Procedure

Following a procedure analogous to the procedure described in Intermediate 14 using {2-chloro-3-[5-(2-chloro-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]phenyl}amine (1.03 g, 2.52 mmol) and 2-furansulfonyl chloride (0.588 g, 3.53 mmol) the title compound of Step E was obtained as an off-white solid (430 mg, 0.735 mmol, 29.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.53 (s, 1H), 8.38 (d, J=5.5 Hz, 1H), 7.91 (d, J=0.9 Hz, 1H), 7.43-7.58 (m, 2H), 7.31-7.43 (m, 1H), 7.08 (d, J=3.5 Hz, 1H), 6.55 (dd, J=3.5, 1.8 Hz, 1H), 6.18 (d, J=5.5 Hz, 1H), 3.71 (t, J=4.8 Hz, 4H), 3.55 (t, J=4.7 Hz, 4H). MS (ESI): 537.96 [M+H]+.

Sources & evidence

ORD record
ord-9e3ea6f93ae44f9e9eef77069ef8c06f
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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