Acetyl chloride → HCID 68753924, compound

HRID 624205Notes

Reaction equation

HRID 624205 reaction equation
C(Cl)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([N:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[O:17])[CH2:7][CH2:6]1.NC1C=C2C(=CC=1)CN(C([NH:39][C:40]1C=[CH:44][C:43]([C:46](=[O:51])NCCC)=[CH:42][CH:41]=1)=O)C2>>[N:39]1[CH:40]=[CH:41][CH:42]=[C:43]([C:46]([N:5]2[CH2:6][CH2:7][CH:8]([O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([N:18]3[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]3)=[O:17])[CH2:9][CH2:10]2)=[O:51])[CH:44]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509898HCID 57509898, compoundHCID 68750133HCID 68750133, compound

Product 1

HCID 68753924HCID 68753924, compound

Procedure

The title compound was prepared as described in Example 278, substituting nicotinoyl chloride for acetyl chloride and N-(3-(piperidin-4-yloxy)propyl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.51-8.70 (m, 2H) 7.75-7.88 (m, 1H) 7.46 (dd, J=7.73, 4.96 Hz, 1H) 7.20-7.38 (m, 3H) 6.28 (t, J=5.35 Hz, 1H) 4.57 (s, 4H) 3.83-4.01 (m, 1H) 3.40-3.63 (m, 6H) 3.16 (q, J=6.35 Hz, 2H) 1.35-1.95 (m, 7H); MS (ESI(+)) m/e 409 (M+H)+.

Sources & evidence

ORD record
ord-ffdaebf43a8746c7a8d8a9c1ed9c1fb0
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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