Acetyl chloride → HCID 57510066, compound

HRID 624180Notes

Reaction equation

HRID 624180 reaction equation
C(Cl)(=O)C.[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:17])[CH2:10]2)#[N:6].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:26]1[CH2:25][CH2:24][CH:23]([CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:16]([N:11]2[CH2:10][C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]#[N:6])[CH:8]=3)[CH2:12]2)=[O:17])[CH2:28][CH2:27]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 68757083HCID 68757083, compound

Product 1

HCID 57510066HCID 57510066, compound

Procedure

The title compound was prepared as described in Example 278, substituting benzoyl chloride for acetyl chloride and 5-cyano-N-(4-(piperidin-4-yl)butyl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.83 (s, 1H), 7.75 (dd, J=7.9, 1.5 Hz, 1H), 7.53 (d, J=7.9 Hz, 1H), 7.41-7.44 (m, 3H), 7.31-7.38 (m, 2H), 6.36 (t, J=5.5 Hz, 1H), 4.60-4.64 (m, 4H), 4.30-4.53 (m, 1H), 3.42-3.71 (m, 1H), 3.02-3.10 (m, 2H), 2.64-3.00 (m, 2H), 1.56-1.84 (m, 2H), 1.37-1.54 (m, 3H), 1.24-1.31 (m, 4H), 0.93-1.16 (m, 2H); MS (ESI(+)) m/e 431 (M+H)+.

Sources & evidence

ORD record
ord-c8ed9993884c497d8d093d939e7a1f98
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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