Acetyl chloride → HCID 57510108, compound

HRID 624183Notes

Reaction equation

HRID 624183 reaction equation
C(Cl)(=O)C.[NH2:5][CH2:6][C:7]1[CH:35]=[CH:34][C:10]([CH2:11][NH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([F:33])[CH:30]=4)[CH2:25]3)=[O:23])=[CH:17][CH:16]=2)=[O:14])=[CH:9][CH:8]=1.NC1C=C2C(=CC=1)CN(C(N[C:49]1[CH:54]=[CH:53][C:52]([C:55](=[O:60])NCCC)=[CH:51][CH:50]=1)=O)C2>>[C:55]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([N:24]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([F:33])[CH:30]=4)[CH2:25]3)=[O:23])=[CH:19][CH:20]=2)=[O:14])=[CH:34][CH:35]=1)(=[O:60])[C:52]1[CH:53]=[CH:54][CH:49]=[CH:50][CH:51]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509629HCID 57509629, compoundHCID 57509898HCID 57509898, compound

Product 1

HCID 57510108HCID 57510108, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and N-(4-{[4-(aminomethyl)benzyl]carbamoyl}phenyl)-5-fluoro-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 9.01 (t, J=6.0 Hz, 1H), 8.83 (t, J=5.9 Hz, 1H), 8.60 (s, 1H), 7.85-7.91 (m, 2H), 7.78-7.83 (m, 2H), 7.63-7.68 (m, 2H), 7.36-7.56 (m, 4H), 7.27 (s, 4H), 7.21-7.26 (m, 1H), 7.10-7.19 (m, 1H), 4.72-4.81 (m, 4H), 4.40-4.48 (m, 4H); MS (ESI(+)) m/e 523 (M+H)+.

Sources & evidence

ORD record
ord-1e6d3c4d1cc8430e9651fe595ffed751
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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