2-Propanesulfonyl chloride → HCID 86701976, compound

HRID 715798Notes

Reaction equation

HRID 715798 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.N1CC(C2C=CC(C(NCC3C=CN4C=CN=C4C=3)=O)=CC=2)C1>>[CH:2]1([S:4]([N:28]2[CH2:29][CH2:30][CH:26]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([NH:18][CH2:17][C:14]4[CH:15]=[CH:16][N:11]5[CH:10]=[CH:9][N:8]=[C:12]5[CH:13]=4)=[O:31])=[CH:21][CH:22]=3)[CH2:27]2)(=[O:6])=[O:5])[CH2:3][CH2:1]1

Participants

4

Reactant 3

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

Product 1

HCID 86701976HCID 86701976, compound

Procedure

The title compound was prepared as described in Example 557C, substituting cyclopropane 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 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.79 (dd, J=9.7, 7.5 Hz, 1H), 3.53 (m, 2H), 3.43 (m, 1H), 3.23 (m, 1H), 2.78 (m, 1H), 2.34 (m, 1H), 2.01 (m, 1H), 0.98 (m, 4H); MS (ESI(+)) m/e 425 (M+H)+.

Sources & evidence

ORD record
ord-e932ec79a2d54580a867600c5ff53080
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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