Acetyl chloride → HCID 57509954, compound

HRID 624128Notes

Reaction equation

HRID 624128 reaction equation
C(Cl)(=O)C.[NH:5]1[CH2:10][CH:9]=[C: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(NC1C=C[C:45]([C:48](=[O:53])NCCC)=[CH:44][CH:43]=1)=O)C2>>[C:48]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:20]3[CH2:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:28]3)=[O:19])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)(=[O:53])[CH2:45][CH2:44][CH3:43]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 57509898HCID 57509898, compoundHCID 57509942HCID 57509942, compound

Product 1

HCID 57509954HCID 57509954, compound

Procedure

The title compound was prepared as described in Example 278, substituting butyryl chloride for acetyl chloride and N-[4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-1,3-dihydro-2H-isoindole-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38 (s, 1H), 7.55-7.58 (m, 2H), 7.27-7.38 (m, 6H), 6.09-6.11 (m, 1H), 4.77 (s, 4H), 4.08-4.14 (m, 2H), 3.58-3.68 (m, 2H), 2.39-2.51 (m, 2H), 2.34 (dt, J=19.8, 7.3 Hz, 2H), 1.46-1.62 (m, 2H), 0.88-0.93 (m, 3H); MS (ESI(+)) m/e 390 (M+H)+.

Sources & evidence

ORD record
ord-5738f0795dd94921bd44acf9ac7d4460
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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