Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 67506102, compound

HRID 1469627Notes

Reaction equation

HRID 1469627 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]([OH:15])=O)=[N:9]2)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:43]([O:45][C:46](=[O:66])[C@@H:47]([CH3:65])[CH2:48][CH:49]([NH2:64])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([Cl:63])[CH:58]=2)=[CH:53][CH:52]=1)[CH3:44]>CN(C=O)C>[CH2:43]([O:45][C:46](=[O:66])[C@@H:47]([CH3:65])[CH2:48][CH:49]([NH:64][C:13]([C:10]1[N:11]=[N:12][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[N:9]=1)=[O:15])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([Cl:63])[CH:58]=2)=[CH:53][CH:52]=1)[CH3:44]

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 135962442-(4-Methoxybenzyl)-2h-tetrazole-5-carboxylic acid2×HCID 67505771HCID 67505771, compound2×

Product 1

HCID 67506102HCID 67506102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methoxy-benzyl)-2H-tetrazole-5-carboxylic acid (Intermediate 32) (149 mg, 0.636 mmol) in DMF (2 mL) is added HATU. The mixture is stirred at room temperature for 15 minutes then (S)-4-amino-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester hydrochloride (Intermediate 31) (200 mg, 0.578 mmol) is added and the mixture is stirred at room temperature for 2 hours. Any insoluble material is filtered and the filtrate is purified by preparative HPLC using a gradient of 10% MeCN/water to 100% MeCN (0.1% TFA) to give (S)-5-(3′-chloro-biphenyl-4-yl)-4-{[2-(4-methoxy-benzyl)-2H-tetrazole-5-carbonyl]-amino}-2-methyl-pentanoic acid ethyl ester; HPLC Retention time 1.79 minutes (condition C): MS 562.4 (M+1).

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. filtrationAny insoluble material is filtered
  3. customthe filtrate is purified by preparative HPLC

Sources & evidence

ORD record
ord-26dacd1963d8455e901bf9caf4649ef7
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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