N,N-Dimethyl-1,3-propanediamine → HCID 25254308, compound

HRID 1880884Notes

Reaction equation

HRID 1880884 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.[CH3:58][N:59]([CH3:64])[CH2:60][CH2:61][CH2:62][NH2:63]>>[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:63][CH2:62][CH2:61][CH2:60][N:59]([CH3:64])[CH3:58])=[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 7993N,N-Dimethyl-1,3-propanediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 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 25254308HCID 25254308, 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 N,N-dimethyl-1,3-propanediamine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16-1.30 (m, 2 H) 1.43-1.57 (m, 3 H) 1.58-1.80 (m, 2 H) 2.67 (m, 6 H) 2.91-3.01 (m, 2 H) 3.20 (br.s., 3 H) 3.22 (m, 2 H) 3.82 (s, 3 H) 4.02 (t, J=13.0 Hz, 2 H) 4.36 (quin., 1 H) 7.39 (d, J=6.1 Hz, 1 H) 7.43 (br. s., 1 H) 8.09 (d, J=8.8 Hz, 1 H) 8.10-8.13 (m, 1 H) 8.31 (br. s., 1 H) 8.50 (br. s., 1 H). [M+H] calc'd for C27H37F2N7O3 546; found 546.

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-53dc581cca1a47498f768639eae3c1bd
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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