Acetyl chloride → HCID 57509967, compound

HRID 624141Notes

Reaction equation

HRID 624141 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=[CH:43][C:42]([C:45](=[O:50])NCCC)=[CH:41]C=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])[CH:42]([CH3:43])[CH3:41]

Participants

4

Reactant 3

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

Product 1

HCID 57509967HCID 57509967, compound

Procedure

The title compound was prepared as described in Example 278, substituting isobutyryl 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 8.40 (s, 1H), 7.59-7.61 (bs, 1H), 7.46 (ddd, J=10.8, 8.5, 2.1 Hz, 1H), 7.30-7.38 (m, 4H), 7.20-7.24 (m, 1H), 4.82-4.87 (m, 2H), 4.76-4.77 (bs, 4H), 4.55-4.60 (m, 2H), 2.78 (h, J=6.9 Hz, 1H), 1.07 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 350 (M+H)+.

Sources & evidence

ORD record
ord-50642067020442d6a173bdcd366d90b8
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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