Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 136245919, compound

HRID 509073Notes

Reaction equation

HRID 509073 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:26])=[C:7]([N:9]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH:23]4[CH2:25][CH2:24]4)=[CH:17][CH:16]=3)=[N:10]2)[CH:8]=1.C[O:28][CH2:29][C:30]([CH3:35])([CH3:34])[C:31](O)=[O:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:26][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:29](=[O:28])[C:30]([CH3:35])([CH3:34])[CH2:31][OH:32])=[CH:8][C:7]=1[N:9]1[C:13](=[O:14])[NH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH:23]3[CH2:25][CH2:24]3)=[CH:17][CH:16]=2)=[N:10]1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 30175063-Methoxy-2,2-dimethylpropanoic acidHCID 136492433HCID 136492433, compound

Product 1

HCID 136245919HCID 136245919, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example-107 by using 1-(5-(aminomethyl)-2-chlorophenyl)-3-(4-(cyclopropylethynyl)phenyl)-1H-1,2,4-triazol-5(4H)-one (0.080 g, 0.228 mmol), DMF (5 mL), 3-methoxy-2,2-dimethylpropanoic acid (0.040 g, 0.342 mmol), BOP (0.151 g, 0.342 mmol), TEA (2.0 mL) to afford 0.010 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.75 (m, 2H), 0.83 (m, 2H), 1.10 (s, 6H), 1.51 (m, 1H), 3.34 (m 2H), 4.31 (br s, 2H), 4.85 (m, 1H), 7.37-7.50 (m, 3H), 7.58 (d, J=7.8 Hz, 1H), 7.77-7.83 (m, 3H), 8.11 (br s, 1H), 12.56 (s, 1H); MS (m/z): 465.07 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-5f8303c9082f4ad68e4b1fac87aadea6
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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