Acetyl chloride → HCID 57509966, compound

HRID 624140Notes

Reaction equation

HRID 624140 reaction equation
C(Cl)(=O)C.[CH2:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]([N:17]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)=[O:16])=[CH:11][CH:12]=2)[CH2:7][NH:6]1.NC1C=C2C(=CC=1)CN(C(NC1C=C[C:42]([C:45](=[O:50])NCCC)=[CH:41][CH:40]=1)=O)C2>>[C:45]([N:6]1[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[C:10]([NH:14][C:15]([N:17]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)=[O:16])[CH:9]=2)[CH2:5]1)(=[O:50])[CH2:42][CH2:41][CH3:40]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509898HCID 57509898, compoundHCID 68754543HCID 68754543, compound

Product 1

HCID 57509966HCID 57509966, compound

Procedure

The title compound was prepared as described in Example 278, substituting butyryl chloride for acetyl chloride and N-(isoindolin-5-yl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.39 (s, 1H), 7.59-7.61 (bs, 1H), 7.43-7.48 (m, 1H), 7.30-7.41 (m, 4H), 7.22 (t, J=7.7 Hz, 1H), 4.77 (d, J=13.9 Hz, 2H), 4.77 (s, 4H), 4.55-4.60 (m, 2H), 2.33 (td, J=7.3, 3.7 Hz, 2H), 1.54-1.63 (m, 2H), 0.93 (td, J=7.3, 1.4 Hz, 3H); MS (ESI(+)) m/e 350 (M+H)+.

Sources & evidence

ORD record
ord-fa3158dcab5149a0afd128afd721dab0
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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