Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178432340, compound

HRID 416435Notes

Reaction equation

HRID 416435 reaction equation
[Cl:1][C:2]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][NH:5][C:6](=[O:30])[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=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.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]([CH3:8])[C:6]([NH:5][CH2:4][C:3]2[CH:31]=[CH:32][CH:33]=[C:34]([F:35])[C:2]=2[Cl:1])=[O:30])[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 178432340HCID 178432340, 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-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-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-9bc2441fb6284ea2964e2eba6a40bd5d
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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