2-Propanesulfonyl chloride → HCID 86701977, compound

HRID 715799Notes

Reaction equation

HRID 715799 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[N:8]1[CH:9]=[CH:10][N:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19](=[O:31])[C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:30][CH2:29][NH:28][CH2:27]4)=[CH:22][CH:21]=3)=[CH:13][C:12]=12.N1[CH2:35][CH:34](C2C=CC(C(NCC3C=CN4C=CN=C4C=3)=O)=CC=2)[CH2:33]1>>[N:8]1[CH:9]=[CH:10][N:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19](=[O:31])[C:20]3[CH:21]=[CH:22][C:23]([CH:26]4[CH2:30][CH2:29][N:28]([S:4]([C:2]5[CH:3]=[CH:35][CH:34]=[CH:33][CH:1]=5)(=[O:6])=[O:5])[CH2:27]4)=[CH:24][CH:25]=3)=[CH:13][C:12]=12

Participants

4

Reactant 3

HCID 824082-Propanesulfonyl chlorideHCID 86701967HCID 86701967, compoundHCID 86701974HCID 86701974, compound

Product 1

HCID 86701977HCID 86701977, compound

Procedure

The title compound was prepared as described in Example 557C, substituting benzene sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.87 (m, 3H), 7.81 (m, 2H), 7.74 (m, 1H), 7.66 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 7.25 (m, 2H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.72 (dd, J=9.8, 7.5 Hz, 1H), 3.46 (m, 1H), 3.26 (m, 2H), 3.11 (m, 1H), 2.17 (m, 1H), 1.78 (m, 1H); MS (ESI(+)) m/e 461 (M+H)+.

Sources & evidence

ORD record
ord-66058064f6f3415bbf3c80cd7ef714cd
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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