Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 25252766, compound

HRID 1880921Notes

Reaction equation

HRID 1880921 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([CH3:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=[N:48][C:43]2[CH:44]=C[CH:46]=[N:47][C:42]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN1CC(N)C1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([CH3:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:48][CH:43]5[CH2:42][N:47]([CH3:46])[CH2:44]5)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

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 57955631HCID 57955631, compoundHCID 670505831-Methylazetidin-3-amine xhydrochloride

Product 1

HCID 25252766HCID 25252766, compound

Procedure

The title compound was synthesized from 4-(9-cyclopentyl-7-fluoro-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and 1-methylazetidin-3-amine hydrochloride. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.65 (m, 5 H) 1.65-1.88 (m, 4 H) 1.88-2.01 (m, 1 H) 2.92 (dd, J=4.7, 2.4 Hz, 3 H) 3.28 (s, 3 H) 3.95 (s, 3 H) 4.01-4.25 (m, 2 H) 4.31-4.55 (m, 2 H) 4.64-4.89 (m, 2 H) 7.44-7.63 (m, 2 H) 8.21 (d, J=8.3 Hz, 1 H) 8.18 (s, 1 H) 8.97-9.09 (m, 1 H) 9.78 (br. s., 1 H). [M+H] calc'd for C26H34FN7O3, 512; found 512.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base

Sources & evidence

ORD record
ord-dd48e477947642bd95ac888490b0f0d3
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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