Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 59737232, compound

HRID 1907698Notes

Reaction equation

HRID 1907698 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([OH:28])=O)=[CH:20][CH:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[NH2:29][C:30]1[CH:35]=[C:34]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)[CH:33]=[CH:32][C:31]=1[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:29][C:30]3[CH:35]=[C:34]([C:36]4[S:37][CH:38]=[CH:39][CH:40]=4)[CH:33]=[CH:32][C:31]=3[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:28])=[CH:20][CH:19]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 86620425HCID 86620425, compound

Product 1

HCID 59737232HCID 59737232, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of acid 40 (0.10 g, 0.25 mmol), amine 4 (72.7 mg, 0.25 mmol) and BOP reagent (0.133 g, 3.0 mmol) in pyridine (2 mL) was stirred 18 h at room temperature. The reaction mixture was concentrated and the residue was purified by flash chromatography (eluent: 1:1 hexane:AcOEt) to give title compound 41 (0.14 g, 61% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography (eluent: 1:1 hexane:AcOEt)

Sources & evidence

ORD record
ord-f2d27d17b3f34548bbbe94ecb6f63e9d
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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