Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-(2-hydroxyethyl)piperidin-4-yl)-3-methoxybenzamide

HRID 914183Notes

Reaction equation

HRID 914183 reaction equation
[CH:1]1([N:7]2[CH2:13][C@:12]([F:16])([CH:14]=[CH2:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]3[CH:19]=[N:20][C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:8]2=3)C[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.[NH2:59][CH:60]1[CH2:65][CH2:64][N:63]([CH2:66][CH2:67][OH:68])[CH2:62][CH2:61]1>>[CH:1]1([N:7]2[CH2:13][C@:12]([F:16])([CH:14]=[CH2:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]3[CH:19]=[N:20][C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([NH:59][CH:60]5[CH2:65][CH2:64][N:63]([CH2:66][CH2:67][OH:68])[CH2:62][CH2:61]5)=[O:29])=[CH:26][C:25]=4[O:33][CH3:34])=[N:22][C:8]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 157334452-(4-Aminopiperidin-1-yl)ethan-1-olHCID 67117829(R)-4-(9-cyclohexyl-7-fluoro-7-vinyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Product 1

HCID 25253228(R)-4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-(2-hydroxyethyl)piperidin-4-yl)-3-methoxybenzamide

Procedure

The title compound was synthesized from (R)-4-(9-cyclohexyl-7-fluoro-7-vinyl-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 2-(4-aminopiperidin-1-yl)ethanol. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47-2.14 (m, 15H) 2.38 (t, J=6.32 Hz, 3H) 2.89 (d, J=11.62 Hz, 2H) 3.28 (s, 3H) 3.49 (q, J=6.23 Hz, 2H) 3.67-3.85 (m, 3H) 3.94 (s, 3H) 4.37 (t, J=5.43 Hz, 1H) 4.89 (d, J=8.34 Hz, 1H) 5.28-5.48 (m, 2H) 6.01 (ddd, J=17.56, 12.76, 10.86 Hz, 1H) 7.40-7.54 (m, 2H) 7.82 (s, 1H) 8.10 (d, J=7.58 Hz, 2H) 8.30 (d, J=8.34 Hz, 1H). [M+H] calc'd for C30H40FN7O4, 582. found 582.

Workup

  1. customas described in the General procedure for amide bond synthesis

Sources & evidence

ORD record
ord-fa694939af48452f999c16454723cd8b
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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