Acetyl chloride → HCID 57511051, compound

HRID 624285Notes

Reaction equation

HRID 624285 reaction equation
C(Cl)(=O)C.[NH:5]1[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])[CH2:6]1.NC1C=C2C(=CC=1)CN(C(N[C:38]1[CH:43]=[CH:42][C:41]([C:44](=[O:49])NCCC)=[CH:40][CH:39]=1)=O)C2>>[C:44]([N:5]1[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])[CH2:6]1)(=[O:49])[C:41]1[CH:42]=[CH:43][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509898HCID 57509898, compoundHCID 68752719HCID 68752719, compound

Product 1

HCID 57511051HCID 57511051, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and N-(4-(azetidin-3-yl)butyl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ 7.67-7.57 (m, 2H), 7.57-7.39 (m, 3H), 7.39-7.23 (m, 4H), 6.28 (s, 1H), 4.56 (s, 4H), 4.34 (t, J=8.3 Hz, 1H), 4.11 (t, J=9.0 Hz, 1H), 4.01-3.82 (m, 1H), 3.65 (dd, J=9.8, 5.8 Hz, 1H), 3.07 (dd, J=12.7, 6.8 Hz, 2H), 2.66-2.53 (m, 1H), 1.59 (dd, J=15.3, 7.7 Hz, 2H), 1.51-1.36 (m, 2H), 1.25 (dd, J=13.5, 6.4 Hz, 2H); MS (ESI(+)) m/e 378 (M+H)+.

Sources & evidence

ORD record
ord-09f51b3019f84f248e1d6f6285b514cc
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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