4-Amino-1-methylpiperidine → HCID 25210559, compound

HRID 914189Notes

Reaction equation

HRID 914189 reaction equation
[CH:1]1([N:6]2[CH2:12][C@:11]([F:15])([CH:13]=[CH2:14])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[C:31]([O:32][CH3:33])=[CH:30][C:26]([C:27](O)=[O:28])=[C:25]([F:34])[CH:24]=4)=[N:21][C:7]2=3)[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]([CH3:66])[CH2:62][CH2:61]1>>[CH:1]1([N:6]2[CH2:12][C@:11]([F:15])([CH:13]=[CH2:14])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[C:31]([O:32][CH3:33])=[CH:30][C:26]([C:27]([NH:59][CH:60]5[CH2:65][CH2:64][N:63]([CH3:66])[CH2:62][CH2:61]5)=[O:28])=[C:25]([F:34])[CH:24]=4)=[N:21][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57955565HCID 57955565, compound

Product 1

HCID 25210559HCID 25210559, compound

Procedure

The title compound was synthesized from (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)-2-fluoro-5-methoxybenzoic acid as described in the general procedure for amide bond synthesis using HATU and 4-amino 1-methylpiperidine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.19-1.90 (m, 8H) 2.05 (dd, J=4.29, 1.52 Hz, 4H) 2.16-2.28 (m, 2H) 2.34 (s, 3H) 2.83 (br. s., 2H) 3.39 (s, 3H) 3.69-3.89 (m, 2H) 3.96 (s, 3H) 4.00-4.10 (m, 1H) 4.97 (quin, J=8.46 Hz, 1H) 5.37 (d, J=11.12 Hz, 1H) 5.50 (dd, J=17.30, 1.89 Hz, 1H) 6.02 (ddd, J=17.30, 14.53, 10.86 Hz, 1H) 6.67 (d, J=7.07 Hz, 1H) 7.56 (d, J=7.07 Hz, 1H) 7.76 (s, 1H) 7.96 (s, 1H) 8.37 (d, J=15.16 Hz, 1H), [M+H] calc'd for C29H37F2N7O3 570. found 570.

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-73fe29a8421a4d57ba4e390b8f459c0a
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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