Acetyl chloride → HCID 57510023, compound

HRID 624171Notes

Reaction equation

HRID 624171 reaction equation
C(Cl)(=O)C.[NH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH: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][CH2:7][CH:8]([C:11]2[CH: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)[CH2:9][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 57510019HCID 57510019, compound

Product 1

HCID 57510023HCID 57510023, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and N-[4-(piperidin-4-yl)phenyl]-1,3-dihydro-2H-isoindole-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.29 (s, 1H), 7.47-7.50 (m, 2H), 7.41-7.47 (m, 5H), 7.34-7.38 (m, 2H), 7.29-7.33 (m, 2H), 7.16-7.18 (m, 2H), 4.75-4.76 (bs, 4H), 4.54-4.64 (m, 1H), 3.57-3.74 (m, 1H), 3.02-3.21 (m, 1H), 2.79-2.93 (m, 1H), 2.75 (tt, J=11.9, 3.4 Hz, 1H), 1.68-1.88 (m, 2H), 1.54-1.63 (m, 2H); MS (ESI(−)) m/e 424 (M−H)−.

Sources & evidence

ORD record
ord-fabbb337d59f41c78d74482033405316
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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