Water → HCID 73854979, compound

HRID 2121987Notes

Reaction equation

HRID 2121987 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](=[C:15]3[S:19][C:18](=[N:20][C:21]4[CH:22]=[C:23]([NH:30][C:31](=[O:36])[CH2:32][N:33]([CH3:35])[CH3:34])[CH:24]=[CH:25][C:26]=4[NH:27][CH2:28][CH3:29])[N:17]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:16]3=[O:44])[N:12]([CH3:45])[C:11]=2[CH:46]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13](=[C:15]3[S:19][C:18](=[N:20][C:21]4[CH:22]=[C:23]([NH:30][C:31](=[O:36])[CH2:32][N:33]([CH3:35])[CH3:34])[CH:24]=[CH:25][C:26]=4[NH:27][CH2:28][CH3:29])[N:17]([CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:16]3=[O:44])[N:12]([CH3:45])[C:11]=2[CH:46]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 73854977HCID 73854977, compound

Product 1

HCID 73854979HCID 73854979, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above N-(3-{5-[5-(2-azidoethoxy)-3-methyl-3H-benzothiazol-2-ylidene]-3-benzyl-4-oxothiazolidin-2-ylideneamino}-4-ethylamino-phenyl)-2-dimethylaminoacetamide (0.34 mmol) in THF (13 mL) was added triphenylphosphine (100 mg, 380 mmol) and H2O (20 mL). The solution was stirred 48 h at room temperature. The solvent was removed under reduced pressure, and the crude material was chromatographed (silica gel, 0-5% MeOH/DCM) to afford the title compound (157 mg, 72% overall).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material was chromatographed (silica gel, 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-3601962d3eee4acc8faac120c03676da
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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