Cyclopropylamine → HCID 25254939, compound

HRID 914130Notes

Reaction equation

HRID 914130 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=NC2[CH:45]=[CH:46][CH:47]=[N:48]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>>[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:48][CH:47]5[CH2:45][CH2:46]5)=[O:29])=[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

Participants

4

Reactant 3

HCID 69828CyclopropylamineHCID 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 25254939HCID 25254939, 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 cyclopropylamine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.50-0.61 (m, 2H) 0.70 (dd, J=7.07, 2.27 Hz, 2H) 1.31-1.48 (m, 2H) 1.51-1.70 (m, 4H) 1.71-1.91 (m, 4H) 2.81 (dt, J=7.14, 3.63 Hz, 1H) 3.17 (s, 3H) 3.93 (s, 3H) 4.03 (q, J=7.07 Hz, 2H) 4.46 (t, J=11.62 Hz, 1H) 7.40-7.55 (m, 2H) 7.90 (s, 1H) 8.21 (s, 1H) 8.26 (d, J=8.34 Hz, 1H) 8.37 (d, J=3.79 Hz, 1H). [M+H] C25H30F2N6O3 calc'd for, 501. found 501.

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-05d2c28528ea406aa514107c4e8750a8
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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