Acetyl chloride → HCID 57511052, compound

HRID 624286Notes

Reaction equation

HRID 624286 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[CH:22]=[CH:21][N:20]=[CH:19][C:18]=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[CH:22]=[CH:21][N:20]=[CH:19][C:18]=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 68748645HCID 68748645, compound

Product 1

HCID 57511052HCID 57511052, 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)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.46 (d, J=5.0 Hz, 1H), 7.67-7.55 (m, 2H), 7.55-7.34 (m, 4H), 6.37 (t, J=5.5 Hz, 1H), 4.60 (d, J=2.3 Hz, 4H), 4.35 (t, J=8.3 Hz, 1H), 4.11 (t, J=9.1 Hz, 1H), 3.96-3.83 (m, 1H), 3.65 (dd, J=9.7, 5.7 Hz, 1H), 3.07 (dd, J=12.8, 6.7 Hz, 2H), 2.65-2.53 (m, 1H), 1.59 (dd, J=15.2, 7.6 Hz, 2H), 1.43 (dd, J=14.4, 7.2 Hz, 2H), 1.34-1.09 (m, 2H); MS (ESI(+)) m/e 379 (M+H)+.

Sources & evidence

ORD record
ord-11e2520e94a34c7fb3f85effc899b83d
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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