Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 24949602, compound

HRID 625064Notes

Reaction equation

HRID 625064 reaction equation
C[N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[CH3:27][CH:28]1[C:36]2[C:35]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[N:34][CH:33]=[N:32][C:31]=2[CH2:30][S:29]1.C(OC([C:50]1([CH2:53][CH:54]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)[C:55](O)=[O:56])[CH2:52][CH2:51]1)=O)(C)(C)C>C(Cl)Cl>[NH2:2][C:50]1([CH2:53][CH:54]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)[C:55]([N:40]2[CH2:41][CH2:42][N:37]([C:35]3[C:36]4[CH:28]([CH3:27])[S:29][CH2:30][C:31]=4[N:32]=[CH:33][N:34]=3)[CH2:38][CH2:39]2)=[O:56])[CH2:52][CH2:51]1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67459220HCID 67459220, compoundHCID 67459562HCID 67459562, compound

Product 1

HCID 24949602HCID 24949602, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HBTU (0.031 g, 0.081 mmol) was added to a solution of 5-methyl-4-(piperazin-1-yl)-5,7-dihydrothieno[3,4-d]pyrimidine dihydrochloride (0.025 g, 0.081 mmol) and 3-(1-(tert-butoxycarbonyl)cyclopropyl)-2-(4-chlorophenyl)propanoic acid (0.027 g, 0.081 mmol) in DCM (5 mL) and TEA (1 mL). The mixture was stirred at room temperature for 1 hour. The solvent was removed, and the residue was subject to column chromatography, eluted by DCM/MeOH (50:1) to give 3-(1-aminocyclopropyl)-2-(4-chlorophenyl)-1-(4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one (30 mg, 81%). LCMS (APCI+) [M+H]+ 558.1; Rf: 3.35 min.

Workup

  1. customThe solvent was removed
  2. washeluted by DCM/MeOH (50:1)

Sources & evidence

ORD record
ord-08c2f6ef5ac548e7bc2d12896acddf98
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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