Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 25254619, compound

HRID 914122Notes

Reaction equation

HRID 914122 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]([OH:29])=O)=[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.[CH3:58][S:59]([N:62]1[CH2:67][CH2:66][CH:65]([NH2:68])[CH2:64][CH2:63]1)(=[O:61])=[O:60]>>[CH:1]1([N:7]2[CH2:13][C:12]([F:14])([F:15])[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:68][CH:65]5[CH2:66][CH2:67][N:62]([S:59]([CH3:58])(=[O:61])=[O:60])[CH2:63][CH2:64]5)=[O:29])=[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 113558261-(Methanesulfonyl)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 25254619HCID 25254619, 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-(methylsulfonyl)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 1.03-1.35 (m, 3H) 1.47-1.90 (m, 11H) 2.75-2.80 (m, 1H) 2.82 (s, 3H) 3.25 (s, 3H) 3.79-3.86 (m, 1H) 3.88 (s, 3H) 4.08 (t, 1H) 4.36-4.47 (m, 1H) 7.43 (dd, J=8.6, 1.77 Hz, 1H) 7.47 (d, J=1.8 Hz, 1H) 8.09 (d, J=8.3 Hz, 1H) 8.16 (s, 1H) 8.22 (d, 1H) 8.41 (br. s., 1H). [M+H] calc'd for C28H37F2N7O5S 622. found 622

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-a7b0443254a14519a2e612efb04b67a4
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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