Water → HCID 56963504, compound

HRID 2038399Notes

Reaction equation

HRID 2038399 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-a53f17e4c5b04d6e8552cffff09c4a83
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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