Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 11570291, compound

HRID 2220671Notes

Reaction equation

HRID 2220671 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:29])[NH:22][CH2:23][C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:17][C:16]=3[C:30]3[C:31]([C:38]([OH:40])=[O:39])=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].Cl.O1C=C[N:44]=C1NC.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:29])[NH:22][CH2:23][C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:17][C:16]=3[C:30]3[C:31]([C:38]([OH:40])=[O:39])=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)(=[NH:44])[NH2:2]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 53408680HCID 53408680, compoundHCID 69198361HCID 69198361, compound

Product 1

HCID 11570291HCID 11570291, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A. 2′-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methoxy-5′-[(oxazol-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid: A mixture of the compound of Example 15, Part F (75 mg, 0.138 mmol), oxazol-2-yl-methylamine hydrochloride (28 mg, 0.208 mmol) NMM (0.012 mL, 1.10 mmol) and BOP reagent (76 mg, 0.172 mmol) in DMF (1 mL) was stirred at rt over 3 days. Reaction was worked up and product isolated as described for Example 15, Part G to provide the amide (78.3 mg, 91%). LC/MS m/z 625.3 (M+H)+.

Workup

  1. customReaction
  2. customproduct isolated

Sources & evidence

ORD record
ord-2978b96ec28647299637c42b958aec86
Source dataset
uspto-grants-2008_08
Patent number
US07417063B2

Reaction notes

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