Benzylamine → HCID 57510239, compound

HRID 624217Notes

Reaction equation

HRID 624217 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1)#[CH:2].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].Cl.N1(S([N:51]=[N+:52]=[N-])(=O)=O)C=CN=C1.C(N(CC)CC)C>CO.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:21]([N:28]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]3[CH2:13][C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:20]3)=[O:11])=[CH:5][CH:4]=2)[N:52]=[N:51]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 235839821H-Imidazole-1-sulfonyl azide hydrochlorideHCID 23667548Sodium AscorbateHCID 86665082HCID 86665082, compound

Product 1

HCID 57510239HCID 57510239, compound

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of N-(4-ethynylphenyl)isoindoline-2-carboxamide (100 mg, 0.381 mmol), benzylamine (33.2 mg, 0.381 mmol), and sodium ascorbate (15 mg, 0.076 mmol) in methanol (1.9 ml) was treated with 1H-imidazole-1-sulfonyl azide hydrochloride (66.0 mg, 0.381 mmol), copper(II) sulfate pentahydrate (9.52 mg, 0.038 mmol) and triethylamine (63.8 μl, 0.457 mmol). Additional methanol (2 mL) was added and the vial was flushed with nitrogen and stirred for 2 days. The mixture was diluted with water and the resulting suspension was filtered with water washes to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.45 (s, 1H), 7.73 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.9 Hz, 2H), 7.49-7.24 (m, 9H), 5.63 (s, 2H), 4.78 (s, 4H), 1.11-1.00 (m, 1H); MS (ESI(+)) m/e 396 (M+H)+.

Workup

  1. customthe vial was flushed with nitrogen
  2. additionThe mixture was diluted with water
  3. filtrationthe resulting suspension was filtered with water

Sources & evidence

ORD record
ord-a88886e39144468b9705eef05cc2ffd3
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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