Water → HCID 56963504, compound

HRID 403279Notes

Reaction equation

HRID 403279 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)=[O:12])[CH2:7]2)[CH2:2]1.[I-].[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH2:26][N:25]([C:30](N1C=C[N+](C)=C1)=[O:31])[CH2:24][CH2:23]2.CCN(CC)CC.O>C(Cl)Cl>[Br:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH2:26][N:25]([C:30]([N:1]1[CH2:2][CH:3]([NH:5][C@H:6]3[CH2:10][CH2:9][N:8]([C:11]([C:13]4[S:14][CH:15]=[CH:16][N:17]=4)=[O:12])[CH2:7]3)[CH2:4]1)=[O:31])[CH2:24][CH2:23]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67287767HCID 67287767, compoundHCID 86691140HCID 86691140, compound

Product 1

HCID 56963504HCID 56963504, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of compound 1g (di-HCl salt, 105 mg, 0.327 mmol) and compound 1j (162 mg, 0.36 mmol) in CH2Cl2 (2 mL) was added Et3N (0.09 mL, 0.65 mmol). The reaction was stirred room temperature overnight. To the reaction mixture was added water, and the resultant mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5% TEA) gave compound 10 (136 m g). MS m/z (M+H+) 490, 492. 1H NMR (300 MHz, CDCl3): δ 7.90 (m, 1H), 7.54 (m, 1H), 7.31-7.28 (m, 2H), 6.96 (m, 1H), 4.42 (d, J=3 Hz, 2H), 4.31-4.16 (m, 3H), 3.96-3.68 (m, 4H), 3.53-3.40 (m, 3H), 2.83 (m, 2H), 2.12 (m, 1H), 1.84 (m, 1H).

Workup

  1. extractionthe resultant mixture was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5% TEA)

Sources & evidence

ORD record
ord-a596a2339f5d4a9680e8cb1a7fe53cd4
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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