Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178432339, compound

HRID 409864Notes

Reaction equation

HRID 409864 reaction equation
ClC1C(F)=CC=CC=1CN[C:6](=O)[N:7]([C@H:9]([CH2:15][O:16][C:17](=[O:29])[NH:18][C:19]1[N:20]=[CH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:11][C:12]([O-:14])=O)[CH3:8].[Li+].CN(C(ON1N=N[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]1=2)=[N+](C)C)C.[F:54][P-](F)(F)(F)(F)F.[ClH:61].Cl.[CH3:63][C:64]1[NH:65][C:66]2[CH2:71][CH2:70][NH:69][CH2:68][C:67]=2[N:72]=1>CN(C=O)C>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:17](=[O:29])[O:16][CH2:15][C@@H:9]([N:7]([CH2:6][C:50]2[CH:49]=[CH:48][CH:47]=[C:46]([F:54])[C:51]=2[Cl:61])[CH3:8])[CH2:10][CH2:11][C:12]([N:69]2[CH2:70][CH2:71][C:66]3[NH:65][C:64]([CH3:63])=[N:72][C:67]=3[CH2:68]2)=[O:14])[N:20]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57947895HCID 57947895, compoundHCID 178432337HCID 178432337, compound

Product 1

HCID 178432339HCID 178432339, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of lithium (S)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(isoquinolin-3-ylcarbamoyloxy)pentanoate (0.43 mmol) and HBTU (244 mg, 0.64 mmol) in DMF (5 mL) was added 2-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride. The resulting mixture was stirred at RT for 1 h, filtered, and purified on RP-HPLC using a mixture of acetonitrile and water to give (S)-2-((2-chloro-3-fluorobenzyl)(methyl)amino)-5-(2-methyl-6,7-dihydro-1H-imidazo[4,5-c]pyridin-5(4H)-yl)-5-oxopentyl isoquinolin-3-ylcarbamate (182.1 mg, 68% for two steps). LRMS (M+H+) m/z 622.2.

Workup

  1. filtrationfiltered
  2. custompurified on RP-HPLC
  3. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-cf5f8bf8db7946918c3f14e8af4fb0de
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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