Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 70336350, compound

HRID 252872Notes

Reaction equation

HRID 252872 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[S:15][C:16]([C:19](O)=[O:20])=[CH:17][N:18]=3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[NH2:24][C:25]1[CH:30]=[C:29]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[CH:28]=[CH:27][C:26]=1[NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[S:15][C:16]([C:19]([NH:24][C:25]4[CH:30]=[C:29]([C:31]5[S:32][CH:33]=[CH:34][CH:35]=5)[CH:28]=[CH:27][C:26]=4[NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:20])=[CH:17][N:18]=3)[CH2:10][CH2:9]2)=[CH:22][CH:23]=1)#[N:2]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 66894634HCID 66894634, compound

Product 1

HCID 70336350HCID 70336350, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of acid 339 (113 mg, 0.34 mmol) amine 178 (100 mg, 0.34 mmol) and BOP (152 mg, 0.34 mmol) in pyridine (2 mL) was stirred at room temperature overnight. The reaction mixture was concentrated and purified by flash chromatography using gradient eluent 50%-75% EtOAc in hexanes to afford the title compound 340 (96 mg, 47% yield). MS: calc: 600.1; found: 601.3 (M+H)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7e70ce4d05154dc5bf5fb56c79382a95
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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