Furan-2-sulfonyl Chloride → HCID 57989968, compound

HRID 1670983Notes

Reaction equation

HRID 1670983 reaction equation
ClC1N=C(C2SC(C(C)C)=NC=2C2C=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=CC=2)C=CN=1.[Cl:34][C:35]1[C:40]([C:41]2[N:42]=[C:43]([N:53]3[CH2:58][CH2:57][O:56][CH2:55][CH2:54]3)[S:44][C:45]=2[C:46]2[CH:51]=[CH:50][N:49]=[C:48]([Cl:52])[N:47]=2)=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:59].[O:60]1[CH:64]=[CH:63][CH:62]=[C:61]1[S:65](Cl)(=[O:67])=[O:66]>>[Cl:34][C:35]1[C:40]([C:41]2[N:42]=[C:43]([N:53]3[CH2:58][CH2:57][O:56][CH2:55][CH2:54]3)[S:44][C:45]=2[C:46]2[CH:51]=[CH:50][N:49]=[C:48]([Cl:52])[N:47]=2)=[CH:39][CH:38]=[CH:37][C:36]=1[NH:59][S:65]([C:61]1[O:60][CH:64]=[CH:63][CH:62]=1)(=[O:67])=[O:66]

Participants

4

Reactant 3

HCID 2795072Furan-2-sulfonyl ChlorideHCID 57989989HCID 57989989, compoundHCID 57990030N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

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-01f200540f7e4e25aeb80a5b43260f0d
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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