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

HRID 1880960Notes

Reaction equation

HRID 1880960 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, 8 H) 2.05 (dd, J=4.29, 1.52 Hz, 4 H) 2.16-2.28 (m, 2 H) 2.34 (s, 3 H) 2.83 (br. s., 2 H) 3.39 (s, 3 H) 3.69-3.89 (m, 2 H) 3.96 (s, 3 H) 4.00-4.10 (m, 1 H) 4.97 (quin, J=8.46 Hz, 1 H) 5.37 (d, J=11.12 Hz, 1 H) 5.50 (dd, J=17.30, 1.89 Hz, 1 H) 6.02 (ddd, J=17.30, 14.53, 10.86 Hz, 1 H) 6.67 (d, J=7.07 Hz, 1 H) 7.56 (d, J=7.07 Hz, 1 H) 7.76 (s, 1 H) 7.96 (s, 1 H) 8.37 (d, J=15.16 Hz, 1 H), [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-2ce7478ac4b64027ab6d441177984d7a
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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