Acetyl chloride → HCID 68753930, compound

HRID 624132Notes

Reaction equation

HRID 624132 reaction equation
C(Cl)(=O)C.[NH:5]1[CH2:10][CH:9]=[C:8]([C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18]([N:20]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)=[O:19])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.NC1C=C2C(=CC=1)CN(C(N[C:42]1[CH:47]=[CH:46][C:45]([C:48](=[O:53])NCCC)=[CH:44][CH:43]=1)=O)C2>>[C:48]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([N:20]3[CH2:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:28]3)=[O:19])=[CH:15][N:16]=2)[CH2:9][CH2:10]1)(=[O:53])[C:45]1[CH:46]=[CH:47][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509898HCID 57509898, compoundHCID 68750167HCID 68750167, compound

Product 1

HCID 68753930HCID 68753930, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and N-(6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.71 (d, J=2.5 Hz, 1H), 8.61 (s, 1H), 8.01 (dd, J=8.6, 2.2 Hz, 1H), 7.42-7.54 (m, 6H), 7.35-7.39 (m, 2H), 7.29-7.35 (m, 2H), 6.46-6.67 (m, 1H), 4.79 (s, 4H), 4.05-4.32 (m, 2H), 3.77-3.94 (m, 1H), 3.47-3.58 (m, 1H), 2.61-2.65 (m, 2H); MS (ESI(+)) m/e 425 (M+H)+.

Sources & evidence

ORD record
ord-004254199143497abe5349d0bb113fa0
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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