Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 25254304, compound

HRID 914104Notes

Reaction equation

HRID 914104 reaction equation
[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:58][C:59]([F:69])([F:68])[CH2:60][N:61]1[CH2:66][CH2:65][CH:64]([NH2:67])[CH2:63][CH2:62]1>>[CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([NH:67][CH:64]5[CH2:65][CH2:66][N:61]([CH2:60][C:59]([F:69])([F:58])[F:68])[CH2:62][CH2:63]5)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]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 162287221-(2,2,2-Trifluoroethyl)piperidin-4-amineHCID 252536804-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid

Product 1

HCID 25254304HCID 25254304, compound

Procedure

The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and 1-N-(2,2,2-trifluoroethyl)piperidin-4-amine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15-1.44 (m, 4H) 1.55-1.89 (m, 10H) 2.42 (t, J=8.0 Hz, 2H) 2.94 (br. d., 2H) 3.17 (q, J=10.11 Hz, 2H) 3.31 (s, 3H) 3.78 (m, 1H) 3.94 (s, 3H) 4.06 (t, J=13.39 Hz, 2H) 7.47 (d, J=8.0 Hz, 1H) 7.50 (s, 1H) 7.91 (s, 1H) 8.15 (d, J=8.02 Hz, 1H) 8.21 (s, 1H) 8.27 (d, J=8.34 Hz, 1H). Melting point: 213-215° C. [M+H] calculated for C29H36F5N7O3, 626. found 626.

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-92e026cd89894da1baffa88689cb324f
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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