Acetyl chloride → HCID 57510107, compound

HRID 624182Notes

Reaction equation

HRID 624182 reaction equation
C(Cl)(=O)C.[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])=[CH:17][CH:16]=1)=[O:14].NC1C=C2C(=CC=1)CN(C(N[C:46]1[CH:51]=[CH:50][C:49]([C:52](=[O:57])NCCC)=[CH:48][CH:47]=1)=O)C2>>[C:52]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]2[CH2:25][C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:32]2)=[O:23])=[CH:17][CH:16]=1)=[O:14])(=[O:57])[C:49]1[CH:50]=[CH:51][CH:46]=[CH:47][CH:48]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509692HCID 57509692, compoundHCID 57509898HCID 57509898, compound

Product 1

HCID 57510107HCID 57510107, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and N-{4-[(6-aminohexyl)carbamoyl]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.57 (s, 1H), 8.43 (t, J=5.6 Hz, 1H), 8.25 (t, J=5.6 Hz, 1H), 7.81-7.86 (m, 2H), 7.74-7.78 (m, 2H), 7.63-7.67 (m, 2H), 7.41-7.54 (m, 3H), 7.29-7.39 (m, 4H), 4.78-4.79 (bs, 4H), 3.15-3.27 (m, 4H), 1.44-1.64 (m, 4H), 1.19-1.39 (m, 4H); MS (ESI(+)) m/e 485 (M+H)+.

Sources & evidence

ORD record
ord-73c3704199dc4ba3818b24c3d0523226
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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